Vacation Rentals By Owner In Chestertown, MD

$742.95

Breathtaking waterfront home on the Chester River

Chestertown, Maryland, United States

Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated entry past your private pool and extensive landscaping to a spectacular vista sweeping the riverfront. Bring your own boat or simply enjoy the recently updated custom Ipe deck featuring pier and floating dock for easy access to the water. brPrivate beach with walk-in sandy river access is perfect for enjoying provided kayaks (1 adult and 2 child), stand-up paddleboards (2), life jackets included.brbrEnjoy your morning coffee from the expansive screened porch featuring 180-degree views of the beautiful Chester River. Amenities abound with a hot tub on the additional poolside deck, outdoor shower, provided pool floats, pool basketball and two adult bicycles (bring your own helmets). brbrThe completely renovated and beautifully furnished home features a fully-equipped chef’s kitchen, bar seating and table for 8, sectional sofa and additional seating, bar height table, large screen TV, powder room and first floor master bedroom with magnificent en suite master bath and desk area.brbrUpstairs, there are three additional bedrooms (1 K, 1 Q) each with a private and updated full bath and access to a waterfront balcony that spans the home. The bunkroom features two sets of twin bunkbeds with trundles and includes gaming system, TV and comfortable kid-sized seating. brbrTake a short bike ride or walk into historic Chestertown to explore this quaint, historic town. Enjoy the farmer’s market every Saturday, speakeasy, cat café, whiskey distillery, River Packet boat cruise daily, wine and tapas bar, shops and multiple outstanding dining options. Check the town calendar and learn more at www.townofchestertown.com to schedule your visit to take advantage of the many special events held throughout the year. End your day gathered around the firepit to watch the blue herons and ospreys as the sun sets on another day in paradise.brbrAsk about discounted rates for extended stays.brbrProperty information & notes: br- Swimming pool & hot tub open May 1-Oct. 1. Slide is not available for rental use.br- Ample parking for 3-4 vehiclesbr- First floor gas fireplacebr- Gas Grill with provided propanebr- Outdoor firepitbr- Upstairs and downstairs full-size washer and dryerbr- Freshly-laundered sheets & bath and beach towels are provided for your usebr- Starter pack of shampoo, soap and toothpaste providedbr- WiFi throughout propertybr- 4 TV’s with Apple TV and Firestickbr- NO SMOKING INSIDE OR OUTSIDE ON THE PROPERTY – will result in immediate evictionbr- NO PETS br- Please exercise caution when opening and closing the wall of sliding pocket doors. See instructions in welcome packet.br- Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. br- Please respect the neighbors and neighborhood.

Bed

Bath

Sleeps

$331.0

/ Nightly

Private Vacation Home

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown, Maryland, United States

Beautiful 1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturday farmers market. Located on a one way street that is flanked with beautiful historic homes and free on street parking. For those with boats, the home is a short walk to the Chestertown Marina which has a boat ramp and transient slips. Our home is only 2.6 miles from Brittland Manor. Please note there is a ring camera by the front door for security purposes.

Bed

Bath

Sleeps

$302.15

/ Nightly

Apartment

Newly restored apartment in the heart of Chestertown

Chestertown, Maryland, United States

Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/dining area/kitchen Historic character with all modem conveniences, including dishwasher, washer/dryer, TV with AppleTv and high speed wifi internet access. Off street parking for one car on first come first served basis with ample street parking.

Bed

Bath

Sleeps

$729.86

/ Nightly

Private Vacation Home

Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!

Chestertown, Maryland, United States

'Chesapeake Bay Beauty' | Ideal for Family ReunionsbrbrYour Eastern Shore escape awaits at this stunning 5-bedroom, 2.5-bath modern farmhouse. Just steps from Tolchester Marina and minutes from Rock Hall and downtown Chestertown, this light-filled home blends classic charm with a cozy fireplace and open layout. Relax on the wraparound porch, soak in the hot tub, or enjoy a game on the bocce court. Perfect for family reunions or peaceful retreats, it’s the ideal spot to make lasting memories!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 king bedbr- Bedroom 3: 1 king bedbr- Bedroom 4: 1 queen bedbr- Bedroom 5: 2 bunk beds (twin/full)br- Additional Sleeping: 1 portable cribbrbrKITCHENbr- Stove/oven, refrigerator, microwave, dishwasherbr- Drip coffee maker, toaster, spicesbr- Cooking basics, dishware & flatwarebr- Island w/ bar seating, high chairbrbrINDOOR LIVINGbr- Ample entertainment space (ideal for reunions & coastal retreats)br- Smart TVsbr- Electric fireplacebr- Hardwood floors, open layoutbr- Board games, booksbrbrOUTDOOR LIVINGbr- Hot tub/cold plungebr- Porch swing, private bocce ball court, bicyclesbr- Expansive wraparound porchbr- Spacious yard surrounded by trees for privacy and tranquilitybr- Plenty of seating for lounging & diningbrbrGENERALbr- Central heating & A/C, ceiling fansbr- Washer/dryer, iron/boardbr- Linens/towelsbr- Complimentary toiletries, hair dryerbr- Free WiFibr- Keyless entrybrbrFAQbr- 1 exterior security camera (facing out)brbrACCESSIBILITYbr- 2-story home, 4 exterior steps to enterbr- 1 bedroom & full bathroom on 1st floorbrbrPARKINGbr- Driveway (10 vehicles)brbr-- THE LOCATION --brbr- 1 block to Tolchester Beach & Marinabr- 5 miles to Rock Hallbr- 10 miles to historic downtown Chestertown’s shops, restaurants, & waterfrontbr- Easy access to boating, fishing, cycling, & Eastern Shore charmbr- 80 miles to Baltimore/Washington Int'l Thurgood Marshall Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 4 exterior steps to enter; the 1st floor includes a bedroom and a full bathroombr- Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device

Bed

Bath

Sleeps

$596.63

/ Nightly

Private Vacation Home

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Chestertown, Maryland, United States

My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened porch & inviting outside patio. Cruise the Chester River with the canoe or two paddle boards provided. Feel free to bring your boat & dock at our deep water pier. Crabbing* (trap & net), fishing (2 rods), & biking (4 provided) are also fun activities to enjoy here at the property. Fire pit (all seasons), indoor fireplace, and outdoor hot tub (available October through the end of April). We will do our best to keep hot tub in working order, but cannot guarantee it will be in working condition 100% of the time. It does take longer to get technicians out here. However we will do our best. We look forward to your stay. All are welcome.br*Crabbing is not as plentiful as years past, and only during the hot summer and early autumn.

Bed

Bath

Sleeps

$454.73

/ Nightly

Cottage

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Chestertown, Maryland, United States

Modern cottage on tranquil large grounds on 20 acres with a pond on one end and a half mile wide creek 800 feet away on the other with a 100 foot dock. Inside a larger historic 18th century farm with original house and buildings. Expansive views. See beautiful sunsets, birds, deer and more. The salt water pool is shared only with the main house on certain dates in the summer. Guests will have the pool area 6 hours a day to themselves (to Oct 1). Recently renovated and furnished. Outside back yard seating and eating area with BBQ. High speed fiber internet, smart TVs. 2 fat tire bikes available. Central AC and heat. Seating on dock and water with fire pit. Easy access, parking, ground floor Master.

Bed

Bath

Sleeps

$220.32

/ Nightly

Private Vacation Home

3 Mi to Washington College! Updated Home w/ Patio

Chestertown, Maryland, United States

Great Birdwatching | 3 Mi to Marina | Day Trip to Rock HallbrbrMorning light, crisp breezes, and a small-town vibe set the tone at this 3-bedroom, 1-bath house. Tucked on a quiet street, the Chestertown vacation rental invites slow mornings on the patio, afternoons exploring the quaint downtown area and riverfront parks, and peaceful evenings back at home. Stylish, calm, and perfectly placed on Maryland’s Eastern Shore — you're invited to experience Chesapeake charm firsthand!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 twin bedbr- Bedroom 3: 1 twin bedbr- Living Room: 1 queen sleeper sofabrbrMAIN FEATURESbr- Smart TVbr- Wood-burning fireplace (bring your own wood)br- Patio w/ dining setbr- Private yard (unfenced)brbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Microwave, toasterbr- Keurig coffee maker (starter coffee provided)br- Cooking basicsbr- Dishware/flatwarebr- Trash bags & paper towelsbrbrGENERAL br- Free WiFibr- Washer & dryer (starter detergent provided)br- Central A/C & heating, ceiling fansbr- Linens/towels, complimentary toiletriesbr- Iron/board, hair dryerbr- Keyless entrybrbrFAQbr- 2 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story home, 3 steps to enterbrbrPARKINGbr- Driveway (6 vehicles)brbr-- THE LOCATION --brbr- Peaceful setting in a scenic neighborhood near the Chester Riverbr- 2 miles to Wilmer Parkbr- 3 miles to Garfield Center for the Arts at the Prince Theatrebr- 12 miles to Rock Hallbr- 17 miles to Eastern Neck Nat'l Wildlife Refugebr- 71 miles to Baltimore/Washington Int'l Thurgood Marshall Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No Pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 3 steps to enterbr- Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the side of the house facing out, and there is a Ring doorbell device with an exterior security camera facing the front outdoor entry. The cameras are outward facing and do not look into interior spaces. The camera records video and sound when activated by motion

Bed

Bath

Sleeps

$360.4

/ Nightly

Country House

Blue Heron Farm Waterfront Chalet

Chestertown, Maryland, United States

About this spacebrRelax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 127 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.brThe spacebrThis chalet-style house was built in 1977, and we’ve recently updated the kitchen, bedrooms and bath.brbrThe main entrance to the house leads into a full-size kitchen with stainless steel dishwasher, electric stove/oven, fridge, filtered drinking water, and cookware. Whether making a pot of coffee or cooking a feast, the kitchen is complete with everything you need to feel right at home.brbrAround the corner from the kitchen is the downstairs bedroom and bath. The bedroom includes a queen sized bed, closet, and a dresser. The downstairs bathroom is a compact design with a shower and small vanity. All linens and towels are included with the house.brbrThe first level also features the great room- an open concept space with floor-to-ceiling windows featuring a living room and dining area overlooking the Chester River. The living room is set up as a cozy gathering space to hang out with your loved ones. The space includes a couch, futon, two chairs, television (with Roku), puzzles, and books. Across the room is the dining area with a large farmhouse table that seats up to 8.brbrThe great room leads to an open staircase that takes you to the second level. This area includes two bedrooms and a full bath. The first bedroom includes a queen-sized bed, closet, dresser, and balcony. The second bedroom includes two extra-long twin beds, a closet, dresser, and balcony. The two rooms share the upstairs bathroom with a large vanity, shower, and bathtub.brbrThe great room also opens up to a wrap-around deck complete with a grill and outdoor seating. This is the spot to catch world-class sunsets!brbrJust a short walk down the path in front of the house leads to a private dock with kayaks available for exploring this beautiful part of the river. The dock can also accommodate shallow-draft boats.brbrThe farm has miles of gorgeous trails for you to enjoy in the spring, summer, and early fall.brbrFinally, the River Chalet is just a 1/4 mile from the home where my wife and I live with our 3 kids. We are on-call if you need us, but otherwise offer total privacy during your stay.brOther things to notebrPlease note the following:br1. At certain times of the year, ticks are abundant in our region. Being in the woods increases your risk of tick exposure. We strongly recommend staying on the property trails, avoiding tall grasses, and using bug spray (specifically on your feet and ankles). For more information, please contact us directly.br2. Because we are out in the country, the house has well water. The water has natural minerals in it including sulfur, which can sometimes emit an odor. This water has been tested and is safe to use, however we provide bottled water for drinking.

Bed

Bath

Sleeps

$569.23

/ Nightly

Private Vacation Home

The Lazy River House

Chestertown, Maryland, United States

Welcome to this freshly renovated, waterfront home on the Chester River. Gorgeous sunsets, picturesque views of the River, endless wildlife… these are just some of our favorite things about this property. Whether you are boating, fishing or just relaxing, The Lazy River House offers tranquilty and the convenience of being close to town, Washington College, Rock Hall, and more!

Bed

Bath

Sleeps

$1345.88

/ Nightly

Private Vacation Home

Historic Manor House on Beautiful Eastern Shore Estate

Chestertown, Maryland, United States

THORNTON Estate, established in 1664, is a quintessential Eastern Shore estate. The magnificent manor house anchors the 325 acre preserved farm outside of Chestertown Maryland. brLord Baltimore granted the original patent for Thornton from colonial lands he received from King Charles I of England in the early 17th century. Conveyed to Philip Hopkins in 1693 the estate is still owned by his direct descendants. The current manor house — built in 1815 — was fully renovated in 2008.

Bed

Bath

Sleeps

$269.26

/ Nightly

Private Vacation Home

River Cottage, Chestertown

Chestertown, Maryland, United States

Relax on the scenic Eastern Shore. We are located just off the Chester River. Step away from the hustle and bustle to our cozy cottage appointed with modern amenities. Our property is enjoyed my families and friends.brOur tranquil backyard offers a fire pit and picnic table for entertainingbrWe have bikes and kayaks for guests to enjoy while they unwindbrbr15 mins from Washington CollegebrbrThe main floor includes a spacious living room, dining room and kitchen.brThe second floor offers (2) spacious bedrooms with a loft that includes the bunk beds.brOutside has a spacious deck with a picnic table and grill that overlooks a patio with a fire pit for guests to enjoy in the evenings.brAdditional entertainment amenities include (2) kayaks, (2) bikes, horse shoes, and fishing poles.brbrGuests utilize self check in to access the cottage.brThe barn stores the additional amenties (kayaks, fishing poles, bikes and fire wood) for safe keeping and easy access.brMinutes down the road you have access to the Chester River and can spend the day paddling with our kayaksbrbrSelf check in for guests. Hosts are available as needed by guests. We are here to help, but not intrude on your trip!brbrRelaxed riverside community

Bed

Bath

Sleeps

$250.87

/ Nightly

Cabin

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown, Maryland, United States

Enjoy the peace and tranquility at Outrange, Blue Heron Farm's recently updated cabin. While we are new to VRBO, we have a 4.94 star rating with over 290 reviews on a different platform. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 127 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm's private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Bed

Bath

Sleeps

$971.46

/ Nightly

Private Vacation Home

The Waterfront Retreat- With Sauna and Hot Tub!

Chestertown, Maryland, United States

Welcome To Paradise! brExperience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. The home features an open layout, spacious living room with sweeping bay views. Enjoy the private guest house, heated pool, private beach and spacious deck for some of the most beautiful sunsets you`ve ever seen. Just minutes from historic downtown, experience comfort with coastal charm—perfect for relaxing, entertaining, or exploring the Eastern Shore.brbrSome days you simply won`t want to leave the house! Enjoy the sparkling pool with lounge chairs. The expansive waterfront porch is the perfect spot for a morning coffee or enjoying the best sunset views on the East Coast. The back patio also includes an outdoor dining area, hot tub, sauna, and the spacious guest house deck. Fire up the grill or black stone for a crab feast, or simply relax as sailboats drift by.brbrWith a quiet neighborhood and some of the most incredible views, this is an ideal spot for a couples’ retreat, family vacation, or friends’ getaway.brbrBRING YOUR BOAT! We are right up the road from Tolchester Marina. They rent slips for an average of $100 per night. brbrThe Property Layout Consists Of The Main Home and a Guest House Next To The Poolbr brTHE INTERIOR SPACE:brbrLightning-fast Wi-FibrLaundry area with washer + dryer (detergent provided)brMultiple sitting areas with plush furniturebrSingle-level main home plus separate guest housebrbrKITCHEN + DINING AREA (Main Home):brbr- Fully-equipped kitchen with cooking + baking essentials (no food)br- Large dining table for 6br- Kitchen island with seatingbr- Stove + ovenbr- Refrigerator + freezerbr- Microwavebr- Dishwasher (detergent provided)br- Coffee maker + mugsbr- Kitchen knife block setbr- Dishes, silverware, glassesbrbrLIVING ROOM:brbr- Smart TVbr- Comfortable sofa and armchairsbr- Throw pillows + blanketsbrbrTHE SLEEPING ARRANGEMENTS – Main Home + Guest House:brbr- Bedroom 1 (Master): King bed with an expansive Bathroom br- Bedroom 2: King Bed + Smart TVbr- Bedroom 3: King Bedbrbr- Guest House (Bedroom 4) Sleeps 4: Open living/sleeping area with pull down Queen bed and pull out sofa, kitchen, full bath, and balcony with water viewsbrbrBATHROOMS – 3.5:br- Bathroom 1: Full bath with walk-in shower, double vanity (In the Master)br- Bathroom 2: Full bath with tub/shower combo (In Between Bedrooms Two and Three)br- Bathroom 3: Full bath with shower (GUEST HOUSE)br- Half bath: Powder room off main living area brbrTHE OUTDOOR SPACE:brbr- Private pool with lounge chairsbr- Spacious deck with dining tablebr- Gas grillbr- Blackstone griddlebr- Expansive lawn with water frontagebr- Parking for multiple vehicles in the drivewaybr- Garage / Arcade Roombr- Changing room for pool usebr- Storage for water toysbr- Outdoor chairsbrbrLOCAL FAVORITES:brbr- Historic Downtown Chestertown – 10 minutesbr- Washington College – 10 minutesbr- Eastern Neck National Wildlife Refuge – 20 minutesbr- Rock Hall (waterfront dining & marinas) – 25 minutesbr- Baltimore – ~1.5 hoursbr- Washington, DC – ~1.5 hoursbrbrThe house, pool, are exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home.brbrA Few Additional Notes:brbr1. Please respect the neighborhood quiet hours from 10PM - 8AMbrbr2. Pool Heat: This property is equipped with pool heat. Heat is turned on from May 1st - May 30th, and again September 1st - 15th and is included with your stay at no extra costs. The temp is set to 80 degrees (or around there). Pool heat does not mean the pool water will be hot it just makes it a comfortable temp to swim in.brbr3. The pool is closed for the Winter between September 15th - May 1st so please be sure to plan your vacation accordinglybrbr4. Upon booking, each guest will receive a guest rental agreement. This must be signed before the House Manual (which includes access instructions for the property) is sent.brbr5. Pet Policy: This property is NOT pet friendly. Please note, if we find evidence of an unauthorized pet in the home, we will ask for it to be removed immediately and guests will be charged a $400 non-refundable fine. This is also grounds for immediate removal of the guests from the home.

Bed

Bath

Sleeps

$656.65

/ Nightly

Private Vacation Home

Escape to Goose Landing: Your Waterfront Retreat in Chestertown!

Chestertown, Maryland, United States

Welcome to Goose Landing, our serene waterfront haven nestled on over three acres along the beautiful Fairlee Creek. We're thrilled to share our secluded 4-bedroom, 2.5-bathroom home with you, offering 350 feet of private waterfront and breathtaking panoramic views.brbrUnwind and explore at your own pace. Enjoy the peace and quiet, gather around the fire pit for cozy evenings, and take advantage of our complimentary kayaks and canoe to explore the tranquil waters. Our private dock is perfect for year-round fun, whether you're into water skiing, kayaking, or fishing. Bringing your own boat Feel free to dock it with us at no extra charge! For some friendly competition, shoot some hoops on our basketball court or enjoy a game of badminton.brbrA Birdwatcher's Paradise!brBirding enthusiasts, you're in for a treat! Fairlee Creek is an incredible spot for birdwatching, teeming with a rich variety of bird species typical of coastal Maryland. Keep an eye out for waterfowl, majestic raptors, and delightful songbirds. We've personally spotted a diverse array of feathered friends, including:br• Red-bellied Woodpeckersbr• Cardinalsbr• Blue Jaysbr• Tundra Swansbr• Bald Eaglesbr• Ospreybr• Baltimore Oriolesbr• Canada Geesebr• Snowy Egretsbr• Wood Ducksbr• Cormorantsbr• Great Blue HeronsbrbrMore Ways to Enjoy Goose Landing!brGoose Landing is the perfect place to practice yoga amidst the calming sounds of nature and stunning waterfront views. Find your flow and rejuvenate your mind, body, and spirit in this peaceful setting.brLooking for an even more immersive outdoor experience We can also accommodate camping on the property, so you can truly connect with nature under the stars.brbrWe are happy to consider special rates for small groups and family reunions, making Goose Landing the perfect destination for your next gathering. We're also happy to help make your stay extra special. Just let us know if you have any special requests.brbrCome experience tranquility and adventure at Goose Landing!brbrThe spacebrbrSleepbrOur spacious home is designed with families in mind, offering four comfortable bedrooms. The primary bedroom, located on the first floor, features a king bed and an attached private bathroom. The remaining bedrooms are upstairs, accessible via a charming spiral staircase. Bedrooms 2 and 3 each have queen beds, while the fourth bedroom is perfect for kids, with a queen bed and two twin bunk beds. An additional bathroom with a tub is also located upstairs.brbrEntertainbrGoose Landing is perfect for family fun and entertaining. The large great room with TV and billiard table is ideal for cozy gatherings. Multiple outdoor deck areas, a screened-in porch, and a patio provide plenty of space to enjoy the fresh air. The expansive yard includes an asphalt play area with a basketball hoop, as well as badminton and pickleball nets (not regulation size) for hours of fun. The well-equipped kitchen, complete with a large breakfast bar, invites everyone to join in the cooking. We even have a piano for our musical guests!brbrLogisticsbrOur driveway accommodates 3-4 cars. For your convenience, the home is equipped with a keypad door lock, and your code will be sent to you the day before check-in.brbrFor those looking to bring boats during their stay, Fairlee Creek Public Landing is 1/4 mile away and you are welcome to dock your boat on our private dock during your stay. The center of the creek can be counted on to have 3 feet at mean low tide. Typically, the average is closer to 4-5 feet in the center and next to our dock is 2-3 feet of depth. Anyone bringing a boat will need to provide proof of insurance.brbrBring your family to Goose Landing for a memorable and fun-filled getaway!brbrGuest accessbrGuests have access to the entire property, including the dock, kayaks, canoe, and sports courts. Please be mindful of our neighbors, as sound carries easily along the waterfront. We appreciate you respecting quiet hours between 10pm -10am. Guests will be required to sign a liability waiver for the use of these amenities. This is not a party house. brbrOther things to notebrWhile we admire and appreciate fury friends, we do not allow them in our home. If this is an issue, we are happy to provide information on pet boarding as an alternative during your stay.brbrThis is our personal vacation home, so you may notice some of our personal belongings around. We kindly ask that you leave them as they are while you are visiting. brbrPlease note that if you cancel a booked reservation, and it is within the timeframe for a full refund, you will receive the refund minus the credit card processing fee of 2.9%.

Bed

Bath

Sleeps

$527.25

/ Nightly

Private Vacation Home

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Chestertown, Maryland, United States

Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for hours on end throughout the year. The home is also located just a short bike ride to Historic Chestertown, or you can even take one of our kayaks in while you enjoy the Chester River's rich wildlife.brbrGuests can also enjoy our pier where you can go crabbing and fishing, or dock your own shallow water boat and use the 8k lb boat lift. We also have a fire pit for you to make cozy fires by the water with plenty of wood for you to enjoy the beautiful evenings. brbrThe three bedroom and two bathroom home features a master bedroom with French doors overlooking the river and a screened in porch to just hang out and watch life go by. The two common areas have plenty of glass doors with spectacular views of the 200+ feet of private shoreline. There is also a giant TV for movies and a foosball table for hours of fun. brbrMinutes from our slice of Heaven you will find Historic Chestertown, founded in 1706, where there is no lack of things to do. Dock the kayaks at Chestertown's public floating dock (or bike or drive over) and explore the brick sidewalks lined with shops, restaurants, art galleries and everything you would expect from a quaint small town. By the way, the whole town is VERY dog friendly!brbrChestertown is also a magnet for traveling foodies. Known for its wealth of Chesapeake cousine, Chestertown is located on the upper Eastern Shore section of the Maryland Crab and Oyster Trail. Visiting the Chestertown Farmers and Artisans market (Saturday mornings), is a great way to acquaint yourself with the local farmers and artisans. For special dietary restrictions you have Figg's Ordinary, and entirely gluten-free cafe. For something stronger, head to Bad Alfred's, featuring house-made spirits, local craft beer and wood-fired pizzas. You can also find 89 Cannon on the river where you can enjoy tranquil water views while eating delicious seafood and other American style food. brbrAbout 20 minutes away, you can find Crow Vineyard. For four straight years, Crow has achieved Maryland Governor's Cup Medal status and gold status at international wine competitions. Also 20 minutes away is the Eastern Neck Island National Wildlife Refuge, which is a 2,285-acre island featuring all kinds of Mid-Atlantic plant and wildlife species. It also has the Duck Inn Trail, a hike that takes you through forests and marsh and arrives at a yet another gorgeous vista overlooking the Chester River. brbrWith so many things to enjoy, book your experience today!brbr**Sheets are provided and beds made, but please bring towels**

Bed

Bath

Sleeps

$1416.19

/ Nightly

Private Vacation Home

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Chestertown, Maryland, United States

Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best of the Eastern Shore. With two main floor bedrooms, including a master suite accompanied with sitting room with full river views. The second main floor bedroom, our Library Bedroom, is spacious and features hardwood floors and built in bookcases. The four large bedrooms on the second floor provide plenty of room to spread out and enjoy. Two of the upstairs bedrooms have their own bathroom, and a jack-n-jill bathroom serves the other two bedrooms.brbrThe main floor living areas are equally built to please - the 33X24 combination LR/DR with hardwood floors and a cathedral ceiling is a great spot for family meals around the 14 person dinner table, and for games, all while looking out at the river. Get closer to the river on the deck, which receives mid-day sun, as well as shade from the large Magnolia adjacent to our home.brbrThe main floor kitchen is fully equipped with a large center island, breakfast dining area, and another set of breathtaking views of the river. The ground floor features a great room with pool table, 75 inch television, and views of the river. brbrPrefer to eat outside The ground floor also includes a substantial screened-in-porch, complete with two ceiling fans, as well as a table with seating for eight that is ready for you. brbrBeyond the many attributes of the house itself, the property features a 110 foot private pier, which is great for launching the kayaks that are provided for your enjoyment (4 single, one double), the paddleboard, swimming, and there is a mooring at your disposal if you want to bring your power boat.brbrAll of this, and you are about a four block walk to historic Chestertown.brbrWe purchased the home in November 2020 from the original (1989) owners, and we love this place! In early 2021 the main entry, LR/DR, MBR, Library bedroom, and all upstairs bedrooms were freshly painted and updated. The furniture in the LR/DR and breakfast room is fresh too. Likewise, the furniture on the ground floor, in the great room and the screened-in porch is all fresh. The pool table in the ground floor great room is a classic, which we purchased from a Chestertown resident, and we had it re-felted in the spring of 2021.brbrThe main floor, primary kitchen is spacious and has served us as a wonderful gathering place, and it has original appliances including an electric stove. The ground floor, secondary kitchen is smaller and functional.brbrOur home is in a wonderful residential neighborhood. Most of our neighbors live in Chestertown year-round. It is important to us to be good neighbors, and so we aim to rent our home to people who want to use it for relaxing, fun vacation getaways - people who will use our home the same way we do. We want and need to be sure that our renters respect our neighbors and avoid any disruptive behavior - things like loud music, other excessive noise, or bright lights, particularly after hours. Likewise, parking is limited to six vehicles, which need to be kept on one of the two driveways. If you are looking for a beautiful home in a great area, with plenty of fun things to do, please come to our River Retreat!

Bed

Bath

Sleeps

$254.14

/ Nightly

Private Vacation Home

Walk to Historic Chestertown: Dog-Friendly Retreat

Chestertown, Maryland, United States

Fenced Backyard | Furnished Deck | Family Game NightsbrbrStep into a storybook at 'Sage Bungalow' in Chestertown, where historic streets and riverside breezes set the scene for adventure. Head downtown to explore local art galleries, enjoy a picnic in the leafy serenity of Wilmer Park, or glide along the Chester River on a boat cruise. After a fun day, retreat to the 2-bed, 2-bath home to cozy up by the fire or settle in for a night of board games. Your Eastern Shore escape awaits!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bed br- Bedroom 2: 1 queen bed br- Living Room: 1 queen sleeper sofabrbrOUTDOOR LIVINGbr- Deck w/ dining space & charcoal grillbr- Covered porch w/ 2 chairsbr- Fenced backyardbrbrINDOOR LIVINGbr- Smart TV, fireplacebr- Dining tablebr- Walk-in shower, shower/tub combo br- Board games, booksbr- Ceiling fans in bedroomsbrbrKITCHEN br- Stove/oven, refrigerator, dishwasherbr- Cooking basics, dishware/flatwarebr- Cuisinart dual coffee maker (drip & single-serve pod, coffee provided)br- Microwave, toaster, blender, ice makerbr- Limited spices (salt, pepper, garlic salt, paprika, tajin, cinnamon & dill weed)brbrGENERAL br- Free WiFibr- Central heating & A/C br- Complimentary toiletries, hair dryer br- Washer/dryer, laundry detergent, hangers br- Linens/towels, trash bags/paper towelsbrbrFAQbr- Pet fee (paid pre-trip) brbrACCESSIBILITYbr- Single-story home, 8 steps to enterbrbrPARKINGbr- Driveway (1 vehicle)br- EV outlet (bring your own charging cable)brbr-- THE LOCATION --brbr- 0.3 miles to Washington College br- 0.5 miles to Historical Society of Kent County br- 0.7 miles to Chestertown Historic District: Chestertown Farmers Market (every Saturday from 8:00 AM to 12:00 PM), Chestertown Tea Party Festival (Memorial Day weekend), parks, restaurants, art galleries, shopsbr- 1 mile to Chester Riverbr- 18 miles to Eastern Neck National Wildlife Refugebr- 67 miles to Baltimore/Washington International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 2 max) br- No events, parties, or large gatheringsbr- Must be at least 18 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 8 steps to enter

Bed

Bath

Sleeps

$1152.02

/ Nightly

Private Vacation Home

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Chestertown, Maryland, United States

Welcome to Lovely Cove Farm. Close to Chestertown and Rock Hall for shopping and dining, but a world away. Secluded and serene spot for birders and boaters and stargazers. Bald eagles, osprey, herons, songbirds and migratory waterfowl can be seen as they go about their daily routines. And a public boat ramp is nearby. Come by boat or land. Enjoy a dip in your private pool before cooking in the gourmet kitchen. Or grilling outside on the gas grill. The skies at night are dark enough to enjoy constellations, meteors and the Milky Way so vividly and memorably.brbrEnter the house and be amazed with the views throughout with large windows overlooking East Langford Creek. There is a lovely living room which opens to the outdoor deck and screened-in porch. The first floor includes the living room, kitchen, dining area, a sitting room, powder room, and an office with a daybed.brbrThe second floors have 2 staircases. The one has the master suite with ensuite bathroom. There is a Queen bed and a daybed. The main staircase takes you up to 3 more bedrooms and a hall full bathroom. Bedroom 2 has 2 twin beds. Bedroom 3 has a king bed, and bedroom 4 has a queen bed.brbrThe pier can be used for fishing or crabbing. Or, to tie up your boat. There is a floating pier which can be used to launch the provided kayaks (2) or canoe. brbrThe pool is for your personal use. Sorry, no daytime guests.

Bed

Bath

Sleeps

$455.8

/ Nightly

Private Vacation Home

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Chestertown, Maryland, United States

brWelcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. With two full bedrooms and bathrooms on the second floor and a cozy third-floor retreat with two twin beds, there is plenty of room for everyone.brbrConveniently located behind the house, you will find three reserved off-street parking spaces. Upon entering the back gate, you'll enter a tranquil courtyard perfect for a barbecue. The screened-in porch leads directly to the well-equipped kitchen, with all the essentials and appliances you need to prepare home-cooked meals.brbrAdjacent to the kitchen, you'll discover two separate relaxation areas, each providing a cozy atmosphere to unwind. A full bathroom is also conveniently located nearby. On the backside of the house is a dining room/living room with a television, offering access to popular streaming services like Netflix, Hulu, and Disney+.brbrOn the other side of the kitchen, you'll find another inviting living room featuring a gas fireplace, creating a warm and cozy ambiance. You'll find the entryway and front door at the end of this living room. Step outside onto the lovely porch, where you can enjoy your morning coffee or evening drinks while taking in the surroundings.brbrHead up the wooden stairway to the second floor, where you'll discover two spacious bedrooms, each with its full bathroom for added convenience. The third floor offers a peaceful retreat with two twin beds for those traveling with children or additional guests.brbrWe invite you to make yourself at home. Experience comfort, convenience, and a relaxing atmosphere during your stay.

Bed

Bath

Sleeps

$1087.88

/ Nightly

Private Vacation Home

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

Chestertown, Maryland, United States

BNB Breeze Presents: Langford Estates!brStep into your very own, secluded 790-acre sanctuary! This 1864 home has been newly renovated to create the ultimate vacation destination for you and your loved ones. This home has everything from a luxurious hot tub, to a coffee bar with a Breville for your morning cup of Joe! The estate includes: brbr- HOT TUB!br- 11-Acre Lake! br- 790 Acres to Roam + Explore! br- 1,600 Square-Foot Deck w/ Lounge Furniture! br- 2 Outdoor Fire Pit Areas br- Indoor AND Outdoor Fireplacesbr- Coffee Bar w/ Breville Espresso Machine br- Outdoor Kitchen!br- Games, and more! brbrThis home was renovated with attention paid to every detail, and it shows! This gorgeous home has large windows that flood in natural light, and cozy places to sit and relax around the indoor wood-burning fireplaces at every turn. Start your day on a soothing note by indulging in a steaming cup of coffee, then nestle into one of our inviting egg chairs on the front porch – it's the ultimate recipe for a relaxing morning. And if you're truly committed to embracing the carefree vacation lifestyle, consider kicking off your day with a refreshing dip in the hot tub, setting the stage for hours of leisure and enjoyment.brbrTHE INTERIOR SPACE:br- Lighting Fast Wi-Fi br- Laundry Room w/ Washer + Dryer (Detergent Provided)br- Gorgeous Design w/ Immaculate Attention to Detail! br- Our home is stocked with clean and sustainable products and toiletries to give you and your loved ones a toxin-free stay! brbrKITCHEN + DINING ROOMbr- Fully-Equipped Kitchen w/ Cooking + Baking Essentials (No Food) br- Beautiful Dining Table that Seats 8br- Kitchen Island w/ 3 Barstools br- Additional Serving Counter, Sink + Coffee Station in Dining Room br- Breville Espresso Machine + Coffee Beans br- Drip Coffee Makerbr- Hot Water Kettle br- Stove + Ovenbr- Fridge + Freezerbr- Dishwasher (Detergent Provided)br- Kitchen Knife Block Setbr- Dishesbr- Silverwarebr- Glasses + Coffee Mugs brbrLIVING ROOMbr- Smart TVbr- Large Plush Sectional Couchbr- Additional Couch + Plush Relaxing Chairs br- Throw Pillows + Blankets br- Wood-Burning Fire Placebr- Large Glass Windows that Flood in Natural Light! br- Additional Sitting Room w/ Second Fireplace brbrTHE SLEEPING ARRANGEMENTS | 4 Bedrooms |br- Bedroom 1: Master Bedroom - King Bed with attached En suite (Full bathroom)br- Bedroom 2: King Bedbr- Bedroom 3: King Bedbr- Bedroom 4: 2 Twin Daybedsbr*Each bedroom includes dreamy mattresses and quality, sustainable linens.brbrBATHROOMS | 2.5 |br- Bathroom 1: Master Bath: Full Bath with deep tub and tile standing shower br- Bathroom 2: Full Bath- Tile Standing Shower (Accessible through the hallway) br- Bathroom 3: Half Bath brbrA meticulously crafted 1,600-square-foot deck beckons, featuring an enticing outdoor kitchen, a bubbling hot tub, a crackling fire pit, and ample seating, all poised to welcome you to extraordinary outdoor living. Gaze upon the serene 11-acre lake! Originally built in 1864, this historic home has been lovingly renovated. Embark on a delightful lake adventure or opt for the cozy comforts of the house, where an array of games awaits your amusement. When the sun dips below the horizon, it's time to gather 'round the fire – and you're spoiled for choice with not just one but TWO inviting fire pits. We've even taken care of the firewood, ensuring that every moment of your evening is filled with warmth and camaraderie.brbrTHE EXTERIOR SPACE:br- HOT TUBbr- Large furnished deckbr- Outdoor kitchen br- Twinkling string lights br- Loungers br- Outdoor dining spaces br- Fire pit seating area br- Outdoor bar with seatingbr- Swinging egg chair br- Loveseatbr- 790 Acres! br- Parking Space for 8 Vehicles! brbrYour stay includes 2 kayaks to take on the water, along with life jackets and paddles. The water access is just a short walk from the house and can be seen right from the back deck. The outdoor fire pit area provides beautiful sunset views and the firewood shed nearby is stocked to help prepare you for a great evening spent outside!brbrWe cannot wait to (hopefully) host you at Langford Creek Estate soon! brbrSEE HOW WE ARE GOING GREEN! brWe love the environment, and are doing everything that we can to minimize our carbon footprint on this area. Here are a few ways that we are loving on the beautiful environment, and welcoming you to join us!br- We use high-quality, sustainable mattresses and linensbr- We offer a drip coffee maker so that you can reduce your single-use pod disposable, while opting for a pot of coffee to eliminate waste!br- All of our toiletries are eco-friendly, clean products that come with reusable dispenser bags to eliminate waste.br- We use LED lighting throughout the home to minimize electricity usage. Thanks to the natural sunshine, you can soak in the sun that floods this home through all of the large windows, without using excessive home lightning during the day!br- Our home is in a great location for Instacart! Make grocery shopping for the family easy while saving on gas!brbrLOCAL AIRPORTS:br1. Wilmington Airportbr2. BWI Thurgood Marshall AirportbrbrLOCAL ATTRACTIONS:br1. Wilmer Park - Beautiful grassy park located right on the water! Take a stroll along the waterfront boardwalk and check out the boats floating by. br2. The Historic District- This district is known for its well-preserved 18th century architecture! br3. Washington College- As one of the oldest colleges in the US, you can explore the beautiful grounds and check for local events held on campus!br4. Chestertown Farmer's Market- One of our favorite things to do on a Saturday morning!br5. Fishing + Crabbing- If you enjoy these activities, there are plenty of opportunities on the Chester River and nearby Chesapeake Bay! brbrLOCAL RESTAURANTS:br1. Play it Again Sam - Delicious bagel sandwiches! Located in our beautiful downtown! br2. Luisa's Cucina Italianabr3. Uncle Charlie's Bistrobr4. The Kitchen at the Imperial br5. Bad Alfred's Distillery br4. Molly's Restaurant (A Favorite!)brbrLOCAL COFFEE:br1. Evergrain Bread Company - this place is an absolute must! It's a small bakery located on one of the older streets of Chestertown. Their pastries are absolutely incredible. If you walk down the street a ways, you will find an open garden. It is a local spot that is open to the public but not well known - a great place to stroll through after grabbing a cup of coffee.br2. Play it Again Sam br3. Figg's Ordinary brbrLOCAL GROCERIES:br1. Harris Teeterbr2. Chestertown Natural Foodsbr3. The Farmer's Market :)br4. Redner's Markets brbrADDITIONAL AMENITIES:br- Linens for each Bedbr- Towels and Washclothsbr- Roll of Paper Towels br- Bottle of Dish Soap br- Trash Bagsbr- Coffeebr- Laundry Detergent br- 2 Rolls of toilet paper, per bathroom br- Bath essentials - Body soap, shampoo & conditionerbr*Please be prepared to bring any additional supplies that you will need. brbrPlease Note:brbr1. Pet Policy: **This property is NOT pet friendly. Please note, if we find evidence of an unauthorized pet in the home, we will ask for it to be removed immediately and guests will be charged a $400 non-refundable fine. This is also grounds for immediate removal of the guests from the home.brbr2. No Smoking: If any signs of smoking are documented, the renter agrees to pay $200.00 / per day.brbr3. Note, we do have a security camera at the home and it is recording 24/7, 365 days a year. It is facing the exterior of the home. There are no cameras inside the home. brbr4. Quiet hours for the property are between 10:00 PM and 8:00 AM. Please keep the noise levels down over this time. brbr5. Upon booking, each guest will receive a guest rental agreement. This must be signed before the House Manual (which includes access instructions for the property) is sent. brbr6. There are NO LONG CHECK-OUT INSTRUCTIONS! We want for you to fully enjoy every minute of your stay! brbr7. We offer 24/7 complimentary communication to ensure that your stay exceeds your expectations! Please feel free to reach out to us day or night, and we will provide you with a swift response!

4

Bed

2

Bath

8

Sleeps

Vacation Rentals By Owner In Chestertown, MD

$742.95

$331.0

$302.15

$729.86

$596.63

$454.73

$220.32

$360.4

$569.23

$1345.88

$269.26

$250.87

$971.46

$656.65

$527.25

$1416.19

$254.14

$1152.02

$455.8

$1087.88

Most popular vacation rentals in Chestertown

$569.23

$320.97

$331.00

$360.40

$399.62

$454.73

$455.80

$525.23

$527.25

$1152.02

Most Popular Cities in Maryland