Vacation Rentals By Owner In Chestertown, MD

A delightful hideaway! Completely remodeled Victorian row house, with four bedrooms, two and a half-bathrooms, a gourmet kitchen, two porches, antiques, rugs, and several writing spaces. Dual zone HVAC, washer & dryer, high-speed internet. Off-street, garage parking with a super-charger and outlet for other electric vehicles.brbrThe main bedroom has a walk-out porch and huge closets. The second bedroom has a high ceiling and comfortable antiques. Two bathrooms are also on the second floor. The third floor has a cool kids/teenager space with three twin beds. The front room has a sofa bed. brbrThe kitchen has a gourmet gas range, warming oven, microwave and collectible china. The spacious living area has a wood stove, and access to a shady porch and small garden with pond.brbrHoliday home for an easy going, busy family of five. Always glad to make new friends from around the world and give suggestions and advice on your trip. Also, always glad to leave you alone to do your own thing.

Victorian Hideaway: Beautiful Exterior, Modern interior

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$525.23

This newly renovated historic home leaves nothing to be desired. Between the beautiful decor, amenities, and location this property has it all!! You can just sit back and relax with family and friends in the large kitchen/family room area or on the back patio. Your are also within 2 blocks of downtown shops, restaurants, and one of the top farmers markets in the state. Come and enjoy this amazing house and location!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$514.66

Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, and decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. All bathrooms have been renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.br** Some dates to consider for fun filled family weeks.brChestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Septbr Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. This whole area is loaded with festivals. Here's a few more.brBettertown days @ Betterton Beach usually the fist weekend in Augbr The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest. brEvery Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.brWilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know. brFeel free to surf the web as well. Most of the local towns have event calendars you can find online.brSpecial winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.brFYI, the school zone has camera 24/7, so watch your speed.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown, Maryland, United States

Bed

2

Bath

6

Sleeps

$158.84

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped with a queen sized bed, linens, washer/dryer, microwave, refrigerator, dinette, toiletries, lux robes... everything you could possibly need to escape the hustle and bustle of life. An additional sleeper sofa, crib, etc. are available at request. Walk to the waterfront or historic district, ride bikes on back country roads. We are more than happy to help arrange paddleboard and kayak adventures! *We require guests to have a verified profile by VRBO OR verification by ID prior to stay*

First Floor Studio Apartment in Historic Chestertown

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$216.24

Escape to our peaceful retreat on Maryland's Eastern Shore, nestled in a quiet, wooded neighborhood near historic Chestertown. The Chesapeake Bay is known for its wildlife and serene landscapes. This cozy haven is perfect for unwinding and reconnecting with nature.brbrAfter exploring Chestertown's charming streets, local shops, and delightful restaurants, or kayaking at nearby Worton Creek, relax in our comfortable home, where you can read, play games, or enjoy the peaceful surroundings.brbrThe spacebrEnter this one-level house into a light-filled sunroom, which leads to a dining room that can seat up to ten people. An open kitchen with island for four and coffee bar is the centerpiece of the house. Off of the kitchen is a fully enclosed family room, with sectional that is comfortable to sleep two. This room includes a 65 inch Samsung Frame TV and bookshelves with carefully curated books - each an all-time favorite of the family that owns the home. This window-filled room gives a view into the bird life that surrounds the property. The master bedroom has a en suite bathroom playfully decorated with fish wallpaper. The McCloskey Room, so named for the children's author whose illustrations from One Morning in Maine adorn the walls, has a twin bed over queen bed bunk, allowing it to be used for a wide array of sleeping configurations. The Garden Room with its soft pink and sage colors hints at an Asian Garden and includes a queen bed. Outside there is an 8-seat picnic table under roof, with ceiling fan and cafe lights. And the rear patio, with a view into the woods, includes a pair of Adirondack chairs and a wood fire pit.brbrGuest accessbrThe whole space is available to guests, with the exception of an owners closet and a rear shed.

Chesapeake Getaway - Marinas - Woodland Views

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$818.87

Ideal for Goose & Deer Hunting Trips | Kayaks Provided | Crab TrapsbrbrCalling all outdoor explorers! Lower your anchor at this 4-bedroom, 4.5-bath vacation rental in Chestertown. With an enclosed porch, a boat dock right on the Chester River, and a basement game room, this spacious abode promises endless family fun! When you're ready to explore, head 1 mile to the Historic District for sightseeing, souvenir shopping, local seasonal events, and of course, the Chestertown Farmer's Market.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 king bed br- Bedroom 3: 2 queen bedsbr- Bedroom 4: 1 twin daybed w/ 1 twin trundle (convertible to 1 king bed)br- Sunroom: 1 queen sleeper sofabr- Game Room: 2 queen futonsbr- Additional Sleeping: 1 portable crib brbrINDOOR LIVINGbr- Flat-screen TVbr- Office w/ L-shaped desk, printer & monitorbr- Furnished sunroom w/ pool viewbr- Dining tablesbrbrOUTDOOR LIVINGbr- Large yard w/ tree swingbr- Enclosed 20' x 40' porch w/ dining areasbr- Charcoal grill (charcoal provided), gas grill (propane provided)br- Seasonal outdoor pool (May 15-September 15)brbrKITCHENbr- Refrigerator, 5-burner stove, ovenbr- Drip/Keurig coffee maker (starter coffee provided), toaster, microwavebr- Cooking basics, trash bags & paper towelsbrbrGENERALbr- Free WiFibr- Central A/C, heat pump w/ electric backup, ceiling fansbr- Iron & board, hangersbr- Linens & towels, hair dryerbrbrFAQbr- Pet fee (paid pre-trip, 3 pets max)brbrACCESSIBILITYbr- Multi-level home, 6 steps to enterbr- Bedroom & bathroom on 1st floorbrbrPARKINGbr- Driveway (8 vehicles)brbr-- THE LOCATION --brbr- Walking distance to a sandy beach along the Chester Riverbr- Under 1 mile to Chestertown's shops, restaurants, schooners & sailing shipsbr- 2 miles to Washington Collegebr- 1 mile to Historical Society of Kent Countybr- 67 miles to Baltimore/Washington International 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- Pet friendly w/ $100 fee (+ fees & taxes, 3 pets max)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This multi-level home requires 6 steps to enterbr- The seasonal outdoor pool is open from May 15 to September 15

Pet-Friendly Home on Chester River w/ Dock!

Chestertown, Maryland, United States

4

Bed

4

Bath

14

Sleeps

$471.75

The privacy of a waterfront home welcomes you to pause and enjoy the beauty of the Chester River. Water views from every window connects you to the flowing water and the expansive outdoors. The southern exposure welcomes spectacular sunrises and sunsets. Relaxation and inspiration is abundant in this buffer zone!brbrLocated close to both Chestertown and Rock Hall, it is an ideal gathering space for families and friends with many activities available in the area. By boat, this energetic space is located near Comegy Byte, the Langford Creek and the Corsica River. There is a boat launch within 1/4 mile of the house and a boat slip at the house; water depth is 2.5 feet MLT. Fishing from the 70 ' dock does not require a license. brbrFor outside gathering, there is a large deck by the water with tables for dining, a picnic table under the shade of a holly tree and a water view bistro table and pergola beside the house. brbrFor cooking, you can enjoy our amazing chef's kitchen with single oven, dishwasher, and fully stocked with dishes and utensils, including toaster and coffee/tea bar. You can also cook outside on our gas grill or charcoal grill. If dining inside, you can entertain guests at our kitchen table/dining bar or enjoy the water views at our second dining table. brbrFor relaxation and amenities, we have a fantastic living room and dining area with water views, full size washer and dryer, 2 TVs with Direct TV, high speed internet, books, games and more! We also have an outdoor fire pit and indoor fireplace for entertaining. Firewood is available for your use.brbrWe provide kayaks and paddle boards for you to enjoy the water around the property. We also have bicycles for you to explore the surrounding landscape. A few crab pots are available to try your luck for the famous Maryland blue crab. Bring your own fishing gear to fish directly from our private pier!brbrThree large bedrooms. Entry level bedroom has a king bed with two single day beds. En suite bathroom with shower and soaking tub. Perfect for families with smaller children.brbrThe second bedroom has a king bed and the third bedroom is a queen. Both have chairs for reading and large closets. One hall bathroom has full bath while the other contains a shower stall. Linens (bed sheets, bath towels and hand towels) are provided with the rental contract. Please contact us if you are interested in opting out of the linen rental during your stay.brbrCome and fall in love with this retreat; return often!brbrKeywords: Self-catering, one-story water front cottage

Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$236.58

“Old Bridge” is a 100-year-old house in a quiet Kingstown section of Chestertown. The house is an American Four Square style home recently renovated from top to bottom. Walk a block to the waterfront or visit the shops, galleries and restaurants close by. This is a no-pet property.brThe spacebrSince it has been completely gutted and revamped, the interior is as a new house. All of the appliances, including cooling and heating, etc. are all new. The kitchen is outfitted with cookware, utensils and dishes. Your bedrooms are well-appointed and each has a chair, should you want to sit and relax. All the mattresses in this house are highly-rated HYPHEN brand which are supportive and comfortable.brGuest accessbrYou will have plenty of parking in an easy-to-turn-around-in lot. You can pull your car right up to the back door to unload luggage with ease. You have full use of the first and second floors of the house.brFree EVIQO EV charging is provided for a guest with an electric car. COMPATIBLE WITH ALL EVs: EVIPOWER electric car home charging stations are equipped with heavy duty rubberized SAE J1772 connector compatible with all EVs / PHEVs in NA: all Tesla models, Chevrolet Bolt, VW ID 4, Nissan Leaf, Polestar 2, Ford Mustang Mach-E, IONIQ 5/6, BMW i3, i4, iX, Mercedes EQS, Audi, Rav4, Jeep Wrangler 4xe level 2 charger (Tesla requires an adapter).brbrOther things to notebrThere will be a guidebook for your convenience when you visit which includes information about attractions and restaurants in our quaint area.

Lovely Home in Chestertown - Free EV Charging for guests

Chestertown, Maryland, United States

Bed

2

Bath

7

Sleeps

$217.56

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!brbrOur guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.brbrWe are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.brbrOur place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.brbrYou'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.brbrThe guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round. brbrSafety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.brbrIn the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.brbrDuring your stay you will have exclusive access to the following rooms and spaces:brbr- Bedroombr- Full bathroombr- Kitchenettebr- Living roombr- Dining areabr- PatiobrbrAdditionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.brbrIf you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.brbrWe're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.brbrHere's what some of our recent guests have said about their stay:brbrPerfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!) - CindybrbrTheir place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place. - MeganbrbrGreat place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out. - JoanbrbrStephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town! - CarlabrbrWe're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you. brbrBook now to secure your spot!

Historic Downtown Garden Oasis with Private Patio

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$253.49

Discover this lovely 2 bedroom and loft gem in Chestertown. This welcoming apartment features 3 queen beds, perfect for a maximum of four guests looking for a comfortable stay. With amenities like AC, WiFi, and a hair dryer, guests can relax and unwind after a day of exploring. Experience what Chestertown has to offer with a stay at our apartment.

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

Chestertown, Maryland, United States

Bed

Bath

4

Sleeps

$207.76

Escape to a secluded, romantic second story studio apartment in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Totally private with views of nature all around, this is the perfect place to relax in front of the fireplace. (Electric, but very cozy and realistic.)brKitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker.brComfortable king bed, kitchenette, and washer dryer. Filtration system for pure delicious drinking water.

Carriage House Hideaway in Middle of Chestertown

Chestertown, Maryland, United States

Bath

2

Sleeps

Exceptional(3)

$320.97

• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in the Chestertown Historic District.brbr• Perfectly positioned to overlook Fountain Park and within walking distance of Washington College and all of downtown Chestertown.brbr• Enjoy unique furnishings that blend early 1900s decor with modern comforts.brbr• Indulge in luxury amenities with priority booking access at Park Row Floats, a renowned exclusive Float Spa located just below the space. brbrPippin’s Retreat offers:brbr• Two bedrooms, each featuring a queen bed.brbr• Two full bathrooms, with the primary bedroom offering an ensuite.brbr• A large, fully-equipped modern kitchen with a view of Fountain Park.brbr• A comfortable living room with characteristic furnishings, opening onto a sizeable back deck - perfect for relaxing or entertaining.brbr• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay.brbrGuest accessbr• You will have the entire third floor to yourself, including the large back deck that provides an elevated view across the historic rooftops of Chestertown.brbr• Access through the rear exterior staircase or enjoy walking up the original historic stairway inside the main front lobby, with its charmingly narrow design reflective of the early era.brbrOther things to notebr• We cherish the building's historic elements and ask guests to be mindful of the unique charm of the narrow staircase.brbr• Visit the Park Row Floats website to make a Spa appointment.brbr• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay. These eco-friendly cleaners leave your space fresh and welcoming, perfect for guests with sensitivities or anyone looking to avoid harsh chemicals. Relax knowing your comfort and the planet are prioritized - ideal for Washington College parents cheering on their students!

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Chestertown, Maryland, United States

Bed

Bath

Sleeps

$399.62

Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. br Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It features two master bedroom suites, one on the ground floor. There are three more bedrooms and a secluded yard. Just outside your garden gate is over an acre of manicured gardens to explore. Gas grill on patio brbrOver the years, we have stayed in a lot of vacation rentals, and we know what we need as guests.brbr1. Comfortable beds and furniturebr2. Quality linens and towelsbr3. Limitless hot water br4. Well-equipped kitchen (hate buying br corkscrews!)br5. Peace and privacy, but security in knowingbr someone is always available.br6. CLEAN, CLEAN, CLEAN.brbrOur goal is to give you the experience we would want to have. To maintain quality control we do our own cleaning, and we are available 24/7 if you should need anything, but will be invisible otherwise.brThe entire house and fenced yard is yours, as well as the large gardens, which are right outside the back gate. We might be doing some gardening in the large garden, but will keep our distance.

Country Estate in Historic District

Chestertown, Maryland, United States

5

Bed