Vacation Rentals By Owner In Annapolis, MD

$712.5

Beautiful Waterfront Townhome In Historic Annapolis

Annapolis, Maryland, United States

This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minute walk to downtown, restaurants, shopping, bakery, and the Naval Academy. brStainless steel appliances, granite countertops, hardwood and marble flooring, gas grill on the patio. Sheets, blankets, body wash, spices/condiments are all supplied as well as two off-street parking spaces.brPool open from Memorial Day to Labor Day.brBooked for 2025 Commissioning Week.br*Please note- Commissioning week we ask for a 7-night minimum stay. Please feel free to contact us for more information.brSorry, no pets are allowed.

3

Bed

3

Bath

8

Sleeps

$1190.46

/ Nightly

Private Vacation Home

Spacious home with an outdoor pool, screened porch, washer/dryer & central AC

Annapolis, Maryland, United States

Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for groups with children, thanks to the various children's sleeping options. It offers a large heated, saltwater pool, and quality furnishings, while is just minutes outside downtown Annapolis. A quick stroll down the street takes you to Thomas Point Park.brbrThis private retreat offers a large new deck, screened porch, fenced saltwater pool, and a sprawling yard for your enjoyment.brbrStep inside to an open and light-filled space. The home features a large updated kitchen and spacious living and dining areas accented with a gorgeous stacked stone fireplace. A seated breakfast bar, lots of counter space, and quality appliances provide you with everything you need and beyond to create and enjoy dinner.brbrTHINGS TO KNOWbrThe pool is open from May 20 until Labor Day.brGuests must use their own accounts to access streaming services.brNo events or parties are allowed on the property due to strictly enforced HOA/community guidelines.

Bed

Bath

Sleeps

$718.42

/ Nightly

Private Vacation Home

Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D

Annapolis, Maryland, United States

Overlooking Chesapeake Bay, this charming Annapolis home is nestled in the serene Bay Ridge community, just steps away from a private beach. Bring the whole family together and relish watching gorgeous sunrises and sunsets and taking in panoramic bay views from both levels of this home's wraparound porches. When you aren't lounging and watching yellow, pink, and orange hues fill the sky, head for the backyard, where a patio, ample seating, and a gas grill provide the perfect space to host cookouts! The screened, first-level wraparound porch is also a prime location to host crab feasts or barbecues while looking out onto the water.brbrSurrounded by mature landscaping, you will feel right at home when you pull into the driveway of this lovely house. Step inside and instantly notice the bright living area adorned with soft seating and a large TV. The full, well-equipped kitchen provides a pleasant space to play chef amongst the gleaming countertops and stainless steel appliances, whereas the large formal dining table is the perfect spot to eat as a family. brbrThe primary bedroom is a place of pure peace with its sprawling living quarters and spa-like en suite bathroom. Invest in self-care as you sink into the jetted tub or rinse off in the walk-in shower. The additional bedrooms are just as comfortable with their delicate color palettes and soft linens. Other interior perks include a large family room, central air-conditioning, and a private washer/dryer.brbrAnd when you want to get out and explore, check out the Annapolis Maritime Museum, Quiet Waters Park, Thomas Point Park, and the Night Hawk Golf Center.brbrTHINGS TO KNOWbrStreaming services are available with guests' own account(s).

3

Bed

3

Bath

10

Sleeps

$955.01

/ Nightly

Private Vacation Home

Updated historic home with parking; near Academy, college & harbor - central AC

Annapolis, Maryland, United States

Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, and the Naval Academy, this historic home is the perfect home base for an exciting and memorable trip to Annapolis! This retreat was built in 1900 and renovated in 2018 with all new furniture (2019). brbrThe enclosed and private patio offers a large sectional for enjoying the garden patio and dining for six. A propane grill will be perfect for warm-weather barbecues! Inside, the living area features a modern sofa with three chairs to lounge and a large smart TV to stream your favorite series. Gather here to binge-watch movies or series or play games of cards. The adjoining dining table seats six people comfortably plus four extra stools at the kitchen island. The kitchen is a show-stopper! It's complete with modern, stainless steel appliances and every cookware you could ever need to prepare mouth-watering meals for the gang. brbrTHINGS TO KNOW

4

Bed

2

Bath

8

Sleeps

$1411.64

/ Nightly

Private Vacation Home

3-story, dog-friendly home near beaches with home theatre, grill & gaming tables

Annapolis, Maryland, United States

Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' historic downtown area, this roomy home will be perfect for a memorable family vacation! There are warm and inviting social rooms for gathering, quiet nooks for some me-time, and sprawling outdoor spaces. The large deck overlooking the lawn into a wooded area offers a very private and serene setting. A sizeable outdoor table with seating and a gas grill is perfect for warm-weather barbecues and meals alfresco.brbrThe spacious living room is adjacent and open to the kitchen with big, comfy furnishings. The sitting area off of the kitchen has more comfortable furnishings and a big-screen TV. The inviting den has leather furnishings and a TV. The open and updated kitchen features a full Sub Zero refrigerator and a full Sub Zero freezer, a fantastic island for prepping, and all the amenities. A separate dining room has seating, the kitchen table provides additional seating, and the kitchen island has stools.brbrThere is a big game room on the lower level with a pool table, air hockey, and foosball table. Adjacent to that is a huge room with a beautiful big bar, stage, and an impressive home theater. Additional perks include free WiFi, Comcast Xfinity cable TV, and a Sonos music system throughout the home.brbrTHINGS TO KNOW

6

Bed

5

Bath

15

Sleeps

$1679.59

/ Nightly

Private Vacation Home

Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill

Annapolis, Maryland, United States

Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience on Spa Creek. Four painstakingly renovated floors bring this home into this century without losing the shipbuilding history that surrounds it.brbrThe photos truly do not describe this incredible home. Walk into the front door into the street-side formal living room on the main level - comfortable and cozy. Pass through the formal dining room to a magnificent loft-type sitting room that opens to the lower-level sitting room. Floor-to-ceiling, two stories of windows bringing the glimmering Spa Creek inside! Wander down the waterside staircase (there are two, one at the main entrance and this one) into yet another comfy lounge space. The lower level sitting room sits beneath the main level sitting room and shares the splendor of two-storied windows. Proceed into the family room and enjoy the big comfy seating looking out to the patio. There is also a beautiful big dining table here.brbrThe kitchen is a large space off of the family room with an island and casual dining table embraced by a fireplace. Unique tile work, lots of counter space, and quality appliances provide you with everything you need and beyond to create and enjoy a family dinner. It features a gas stovetop, oven, microwave, large double-door refrigerator with drawer freezer and drink station, Keurig coffee maker, dishwasher, toaster oven, and all of the pots, pans, and dishware you need for memorable family gatherings.brbrThere are three unique dining areas in this home! The cozy, warm kitchen dining area is perfect for casual dining and offers to seat everyone. The formal dining room on the main level offers beautiful views with pre or post-dinner cocktails on the adjoining balcony. The lower-level family room also boasts a long fabulous dining table for a casual meal and game night.brbrWalk out your doors to the patio, lawn, and water's edge which has a dock for your boat and water toys. From the top down, the main-level balcony features two cushioned chaises and a gorgeous fire table surrounded by more Adirondacks. The lower-level walkout opens to a stone patio with chairs, a lawn, and two deep water docks for your boat and water toys. Additionally, a propane grill is available for warm-weather barbecues.brbrTHINGS TO KNOW

4

Bed

4

Bath

10

Sleeps

$848.11

/ Nightly

Private Vacation Home

Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D

Annapolis, Maryland, United States

Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend most of your time on the rocking chairs or comfy outdoor couch taking in the Chesapeake Bay. The back patio and gardens offer alfresco dining with a gas grill and a beautiful teak umbrella table with seating for six.brbrThe warm living area looks out to the Bay with a large comfy couch, swivel chairs, and a gas fireplace. Spend relaxing evenings on the amazing stone porch with Adirondack rockers - take in the famous Annapolis sailboat races from there and the second-floor balcony! The lower-level rec room has a big couch that converts to a queen sleeper, two comfy chairs with ottomans, a game table and four chairs, a large screen TV, and a wet bar. The large and bright kitchen is open to the rest of the main floor for continuous views of the Bay. All top-of-the-line, brand-new appliances, gorgeous cabinetry and surfaces, an eat-in kitchen bar with seating, a prep island with sink, and a wall-mounted kitchen TV. Enjoy your meals at the dining table for 10-12 or dine alfresco on the back deck on the large teak table with an umbrella for shade.brbrTHINGS TO KNOWbrThis home is not appropriate for events due to parking and neighborhood restrictions.

4

Bed

3

Bath

10

Sleeps

$1888.97

/ Nightly

Private Vacation Home

3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace

Annapolis, Maryland, United States

Perfect for family and group gatherings, this darling, three-story home near Severn River is calling your name! There is a beautiful paver patio with a backyard firepit surrounded by a wooded backyard and mature landscaping. Planning on hosting warm-weather barbecues There is a propane grill available for you! The screened porch off the kitchen (main level) features an outdoor dining table for six overlooking the backyard.brbrInside, the beautifully decorated open floor plan is perfect for entertaining and family gatherings. The comfortable family room adjoining the kitchen offers a smart TV, a large sectional sofa, two big and cozy chairs, and a wood-burning fireplace. The formal living room has inviting and comfortable conversational seating. When mealtime comes round, the big, bright cook's kitchen will be perfect for gathering! Some of the incredible appliances include a built-in microwave, Bosch dishwasher, French-door fridge, a JURA automatic espresso/latte maker, and an under-counter nugget ice maker. The eat-in kitchen table seats five and the large island with counter stools seats three. The formal dining room seats up to eight people comfortably! Additional perks include a wine refrigerator and a pantry that connects to the formal dining room.brbrThere is a fully-equipped basement apartment with Bedroom #6, a full bathroom, a fully-equipped kitchen, a full-size washer/dryer, and a living area with a TV and Ping-Pong table. Severn River can be seen from the third-floor loft bedroom depending on the season; water views are only a short walk down the street.brbrTHINGS TO KNOW

6

Bed

6

Bath

12

Sleeps

$1911.14

/ Nightly

Private Vacation Home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Annapolis, Maryland, United States

On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pier will be a place for you and yours to relax and make memories. This beautiful Frank Lloyd Wright-inspired contemporary home with plenty of waterfront amenities boasts renovated interior and exterior spaces. brbrThe kitchen space has been designed to gather friends and family with top-of-the-line amenities for preparing and enjoying a gourmet meal. Two dishwashers and double refrigerators are an entertainer's dream. Use the dumbwaiter to easily send everything up to the third floor for dining with a view. The kitchen features a large island with seating and a dining table. Dine outside under the shade of large umbrellas. The third-floor rooftop has incredible views.brbrThe third-floor loft has an additional sitting area with a TV, a wine cooler, and a refrigerator. A warm, formal living room has a massive fireplace with reclining couches, water views, and a TV. An adjacent sitting room has a gas fireplace and seating with water views. The large covered front porch has big, comfy furnishings to snuggle into and take in the sunrises over the water.brbrEach of the bedrooms has been uniquely outfitted with your comfort in mind. The primary bedroom features a gas fireplace and water views, while one guest bedroom boasts bay views and an en suite bathroom.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brThe pool is open from May 20 until Labor Day.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.

6

Bed

4

Bath

12

Sleeps

$731.68

/ Nightly

Private Vacation Home

Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf

Annapolis, Maryland, United States

Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great walkability to the area's restaurants, art galleries, shops, parks, and water taxi - fun in the sun is inevitable! brbrOn days you don't want to go far from your stay, sit and enjoy the pleasant Maryland weather from the sprawling deck while grilling or around the firepit.brbrInside, you'll instantly take notice of the cozy living room adorned with soft seating and a large TV. The well-equipped kitchen presents a lovely space to play chef when you aren't dining out. And when it's time to eat, whether with a home-cooked meal or takeout, gather at the formal dining table. brbrAll bright, airy, and simply decorated - the bedrooms are places of peace. Also, inside, you will appreciate having access to a private washer/dryer and central air-conditioning. brbrAs evening nears, sip on your favorite drink with your loved ones in the yard as you cheers to beautiful memories! brbrTHINGS TO KNOWbrStreaming services are available with guests' own account(s).

4

Bed

2

Bath

10

Sleeps

$452.4

/ Nightly

Private Vacation Home

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

Annapolis, Maryland, United States

Historical charm meets modern convenience at this darling brick home, within easy walking distance of all Annapolis' charms. Situated directly across from historic St. Johns College and a few blocks from the U.S. Naval Academy, you'll be steps away from all of downtown's shops, restaurants, bars, historical landmarks, Annapolis City Dock, and more. Spend the day shopping at Maryland Avenue's antique shops and bring home some history of your own, or while away an afternoon at one of many waterfront restaurants.brbrAt home, watch the world go by each morning with coffee on your shady-fenced patio, then step inside the full kitchen to make some breakfast. Throughout the home, you'll find hardwood floors and a quaint, cozy feeling. Spend the evening streaming the latest on the smart TV, or head back out for a night on the town. Rest easy in either the guest room or the primary bedroom upstairs, which takes up the entire floor. All the charms of Annapolis await - all that's left to do is book. brbrTHINGS TO KNOWbrGuests can use personal logins for streaming services.brThe fireplace is for decorative purposes only and is not usable.br*Please note there is on-going construction across the street from this home

Bed

Bath

Sleeps

$756.46

/ Nightly

Private Vacation Home

Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to your Annapolis getaway! Situated on an expansive and rare 1/2 acre homesite, this beautifully preserved home blends historic charm with modern amenities—perfect for families, friend groups, or Navy families visiting town. brbr brbrInside, the main level features two spacious king bedrooms, a full bath, a sun-filled living room, and a delightful four-seasons sunroom—ideal for morning coffee, evening wine, or movie nights on the big-screen TV. brbr brbrUpstairs, you'll find three additional bedrooms, including a generous combo guest room (with an additional sitting room/bedroom). There’s also a shared full bath and a full laundry room. The entire home has recently been updated to include a modern HVAC system with mini splits and remotes in each bedroom and gathering space. brbr brbrSleeping Arrangements 5 Bedrooms, 2 Baths (Sleeps 12): brbrSecond Floor brbrFamily Pink King Bedroom: King bed + Twin plus Twin Trundle brbrTan & White Guestroom: King bed brbrGray Guestroom: King bed brbrFull bath in the Second Floor Hallway brbr brbrMain Floor brbrBlack & White Guestroom: King bed brbrAnchor Guestroom 2: King bed brbrShared full bath on the Main Floor hallway brbr brbrHome Highlights: brbrFully equipped kitchen with stainless steel appliances brbrMultiple hangout spaces with Flatscreen TVs: Living room, and Four-seasons sunroom with flatscreen Smart TV brbrHigh-speed WiFi + 3 large Smart TVs brbrDriveway parking for multiple vehicles brbrWasher/dryer for guest use brbrLuxury linens + complimentary starter toiletries and paper products brbrDog-friendly (with $150 non-refundable pet fee per pet) brbr brbrLocation - Walkable to it all! brbrNavy-Marine Corps Memorial Stadium – 0.7 miles brbrU.S. Naval Academy – 1.8 miles brbrDowntown Annapolis shops & restaurants – 1 mile brbrWashington, D.C. – 32 miles brbrBaltimore – 31 miles brbrSkip the parking hassles and walk to parades, festivals, farmers markets, waterfront events, and cozy cafes. You’ll love being in the heart of it all—without ever needing your car. brbr brbrHouse Rules: brbrPrimary renter must be 25+ brbrNo parties, smoking, or events brbrQuiet hours must be observed brbrCheck-in: 4:00 PM | Check-out: 11:00 AM

Bed

Bath

Sleeps

$655.5

/ Nightly

Private Vacation Home

Lots free parking, hot tub, outdoor oasis - NOT party house

Annapolis, Maryland, United States

Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. It is a close-proximity neighborhood. We live in one half (it is our primary residence but i rent it sometimes to make extra income as a disabled veteran) & someone else lives in other but there's a privacy fence & all amenities listed are ours only. It is an easy walk to all the popular sites. We've unlimited, free parking & many, many amenities. We've lovely deck w/ built-in fireplace, hot tub & relaxing furniture. Backyard is a fantastic, fun place for whole family. There’s ping pong, bocce, cornhole, horseshoes, tic-tac-toe. There's an outdoor bar w/flat screen tv, so you can watch movies or games from hot tub. Upstairs from main level king master bdrm (ensuite w/ full bathroom) , 2 bdrms w/ queens (one w/ a TV) as well as full bath in hall. On main level theres a kitchen w/ small table/chairs, dining w/ seating for 8-10, living area w/electric fireplace, massage chair, sofa, smart TV, bluetooth speakers & enough seating for 10. No bedrooms on main level (must use stairs). There's also a 1/2 bath. Downstairs to lower level is a hall with lots games, books & crafts. 3 rooms on lower level.- a laundry area w/ washer, dryer, extra frig & lots of storage w/ extra pillows, sheets, party supplies, etc. On lower level there’s a room w/ queen bed. 3rd lower level room has two double futons that can be opened as bed for 2 or used by one as is. Theres a small exercise area w/peloton, yoga eqpt, weights,bands, etc. Lots of games, dart board, a music area w/ guitar, keyboards, karaoke , etc. Amenities incl exercise eqpt, peloton, bikes, vitamix, Wi-Fi, several TV's , dining table seats 8, 2 frig/freezers, blankets, coolers, tons games, towels/pillows, picnic stuff, etc. hardwood floors on main/upper floors. We've hosted hundreds in our home & love providing a great vacation experience. This is NOT a party house - it is for nice family gatherings or relaxing getaways w/ few close friends. You many Not have any parties or events without our advance permission - If we get noise complaints we have the right to remove you from the premises. WE WILL NOT TOLERATE UNAUTHORIZED GUESTS OR PARTIES.brbrIMPORTANT INFO - In case of questions/concerns during stay – call/text Laurie 443.994.0835.

Bed

Bath

Sleeps

$387.6

/ Nightly

Private Vacation Home

Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis

Annapolis, Maryland, United States

New Outdoor Space for 2026! Enjoy sunrises on the newly built porch. A great space for morning coffee or to spend an evening outdoors. This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay. Whether you're looking for a place to relax and recharge or to enjoy water sports, this is the place for you. Just a 5 minute stroll and you’re on the beach or curl up and enjoy the cozy interior of this home. Kitchen has everything you need to prepare meals or store leftovers from one of many nearby restaurants. Located on the shores of the Chesapeake Bay, this property is only 5 miles from downtown historical Annapolis and 35 minutes from Washington DC. Just the spot for a relaxing getaway on your own or a fun packed time with family and friends. This community offers a variety of activities from water sports to beach volleyball. Want to keep up with your exercise routine, try our 1 mile, three station exercise circuit course. Want to take your canoe/kayak out, you have access to the water at the boat ramp just a short walk away. A kid and pet friendly neighborhood with playgrounds and doggie stations nearby for your usage. Check out the video for more information about the neighborhood. Welcome home to The Anchors!

2

Bed

1

Bath

4

Sleeps

$1417.8

/ Nightly

Private Vacation Home

Beautiful waterfront home on The Chesapeake Bay with private dock & beach access

Annapolis, Maryland, United States

Find gorgeous gathering spaces inside and out at this light-filled three-story waterfront home on a protected inlet of the Chesapeake Bay. Here in Bay Ridge, you'll have a private dock, access to the bay beaches, and a stunning setting for family vacations and special holidays. You'll be within five miles of historic downtown Annapolis, home to charming shops, great eateries, and the U.S. Naval Academy.brbrSpend sparkling summer days outdoors, where several beautiful spaces await you. Sip your first cup of morning coffee in an Adirondack chair on the deck, taking in a serene view of the bay below. Launch your kayak from the dock, watch your kids play in the gently sloped backyard, and gather for evening barbecues on the shaded patio beneath the deck. One of the guest bedrooms boasts direct patio access.brbrAs you step inside the front door, you'll be greeted by a grand spiral staircase and a wall of windows framing the lake. One of Annapolis' leading interior designers recently renovated the entire home. At the heart of the house is a two-story great room with generous seating, a smart TV, and doors that lead outside to the deck. To one side of the great room sits a formal dining room and a wet bar for entertaining. To the other is an expansive kitchen overlooking the lake with stainless steel appliances, including an in-island gas stove, a light-filled breakfast nook, and a full laundry room. Step into the hot tub and simmer as you relax your body.brbrOther notable features can be found at every turn, including a private home office for remote work, a huge den downstairs with another smart TV and kitchen, a quiet room for yoga, and a fantastic game room with air hockey, foosball, and a game table. brbrTHINGS TO KNOWbrStreaming services are available with guests' own account credentials.brSmoking is prohibited on the property.brThe gas fireplace is not operational.

5

Bed

3

Bath

10

Sleeps

$808.19

/ Nightly

Private Vacation Home

2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

Annapolis, Maryland, United States

Looking for the perfect retreat for a memorable stay-cation with your beloved groups Then, look no further than this two-story, family-friendly home located just a mile from the heart of the forever charming Annapolis! The extensive enclosed backyard provides a private space where you and your guests can hang out and create everlasting memories - gather around the firepit under the starry night sky or host a warm-weather barbecue on the deck, equipped with a propane grill, a six-person dining table, and a cushy swing. brbrUpon entering the first floor of this darling home, guests will first come across a beautifully appointed foyer with vintage music-scene decor. As you continue the tour, an astonishing dining room will appear before your eyes. This space is furnished with a large eight-person dining table. The tiled open kitchen will be a chef's delight. It has stainless steel appliances, including a double-door fridge, stove, oven, dishwasher, drip coffee maker, and microwave. Additional highlights include an elegant wet bar, a wine section, and a breakfast bar that seats three. The adjoining and spacious living room has been equipped with comfortable sofas, a three-piece coffee table set with a chess board, a stone floor-to-ceiling gas fireplace, and a gigantic smart TV with streaming services and a soundbar. brbrAll four bedrooms and a laundry room are upstairs. The carpeted main bedroom offers a comfortable bed and an en suite bathroom with a stand-alone shower with a tiled bench, a soaking tub, and double vanity.brbrTHINGS TO KNOW

4

Bed

3

Bath

8

Sleeps

$496.99

/ Nightly

Private Vacation Home

Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views

Annapolis, Maryland, United States

This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, allowing you to explore all the attractions Annapolis offers. brbrNearby, you'll find popular destinations such as Annapolis City Dock, Rams Head on Stage, and the U.S. Naval Academy Museum. Enjoy strolling along the city's waterfront, watching live music, and exploring historical museum exhibits. brbrThis multi-level retreat features artfully decorated interiors and great outdoor space for entertaining, grilling with friends, or gathering for laughs around the firepit. Not to mention, rooftop access provides incredible views of the surrounding city! The deluxe kitchen boasts stainless steel appliances and ample dining space - perfect for any home chef crafting delicious meals. The bedrooms, furnished with luxurious linens and cozy blankets, offer a comfortable sanctuary for streaming your favorite movies and unwinding after a fun day exploring your new city. brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.

2

Bed

1

Bath

6

Sleeps

$893.59

/ Nightly

Private Vacation Home

Historic downtown townhome with brick courtyard, sunroom & parking

Annapolis, Maryland, United States

Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and friends looking for a convenient location with parking to immerse yourselves in the history of Annapolis. This prime location situates you two blocks from Maryland State House, three blocks from City Dock, and four blocks from USNA. Other great attractions include Watermark Tours, Charters, Cruises, Rams Head On Stage, Banneker-Douglass Museum, Jonas and Anne Catharine Green Park, Quiet Waters Park, and more.brbrThis historic home features living areas that will take you back in time to life in 1900 Annapolis, yet offers basic modern amenities. The kitchen and dining area surround an original brick fireplace with plenty of space and all you need for preparing treats for the crew. The private sunroom with comfy sofas and a desk look out over the brick courtyard. Curl up on the sofa and enjoy a fun book or an entertaining movie or show on the smart TV with cable and streaming. The fully-appointed kitchen has been updated and has all the essentials for you to prepare delicious homemade meals and treats for the crew. Outside, you will discover a small side/backyard for outdoor enjoyment and dining alfresco.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brStreaming is available using your own accounts.brThe wood fireplace is ornamental only and not for guest use.

Bed

Bath

Sleeps

$750.59

/ Nightly

Private Vacation Home

Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrAvailable for Commissioning Week 2025! brbr brbrCharming 1905 Eastport Duplex: Historic Character Meets Modern Comfort brbrStep into a beautifully-preserved piece of history with this charming 1905 duplex in the heart of Eastport. Offering a seamless blend of old-world charm and modern amenities, this home is perfect for families, professionals, or anyone seeking a cozy, yet stylish getaway. brbr brbrMain Floor: The spacious open layout on the main floor includes a large living area, a dedicated office/desk space, and a convenient powder room. The inviting dining area opens to a gourmet kitchen, fully equipped with stainless steel appliances, perfect for cooking up a feast. The main floor also features a private, fenced backyard, ideal for relaxing or entertaining. brbr brbrUpstairs: Two generously-sized King bedrooms provide a restful retreat, complete with luxury linens and a shared full bath. One bedroom boasts a private balcony overlooking the serene backyard and the front King bedroom has its own flatscreen TV and desk space. A bonus loft space offers additional room for kids or younger families to relax and enjoy their own shows. brbr brbrAdditional Features: brbrParking for up to 3 cars brbrPrivate fenced backyard with a patio deck and and gas fire pit brbrCovered front porch, perfect for enjoying the neighborhood brbrGas grill (propane included) brbrHigh-speed WiFi and a big-screen TVs for entertainment brbrDedicated workspaces on each level for remote work or study brbrFull washer & dryer for your convenience brbrDog-friendly brbr brbrPerfect Location: Situated just steps away from Eastport's vibrant cafes, restaurants, and bars, this home offers easy access to everything the neighborhood has to offer. Water access for paddle boarding and kayaking (BYO) is just a short stroll away. brbr brbrPlus, you're only: brbr1.5 miles from the U.S. Naval Academy brbr30 miles from Washington, D.C. brbr25 miles from Baltimore brbr brbrHouse Rules: brbrNo smoking, parties or events brbrDogs ok if $150/per pet fee paid prior to checkin brbrMust be 25+ to book brbrCheck-in: 4:00 pm | Check-out: 11:00 am

Bed

Bath

Sleeps

$561.01

/ Nightly

Private Vacation Home

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Annapolis, Maryland, United States

Pet Friendly w/ Fee | Home Office Space | 7 Mi to United States Naval Academy brbrExperience the best of Maryland when you stay at this 4-bed, 3.5-bath vacation rental. With a lakefront beach, a shopping center, and a sprawling park just a short walk away, this family-friendly home offers plenty to do nearby! Ready to venture out Visit the scenic shores of Sandy Point State Park, enjoy waterfront adventure along the Chesapeake Bay, or explore the charming historic district in downtown Annapolis.brbr-- THE PROPERTY --brbrSTR00593brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 queen bedbrbrOUTDOOR LIVINGbr- Private balcony w/ seatingbr- Back deck, dining space w/ umbrellabr- Fenced-in backyard, charcoal grill (charcoal provided)br- Nearby public lake w/ kayaks & canoesbrbrKITCHENbr- Refrigerator, stove/oven, microwave, hot platebr- Keurig coffee maker (coffee provided), blender, slow cookerbr- Cooking basics, toaster, toaster oven, rice cookerbr- Dishwasher, dishware/flatware, paper towels/trash bagsbrbrINDOOR LIVINGbr- 4 Smart TVs, gas fireplacebr- Bar-top seating, breakfast nook, formal dining roombr- Dedicated office space, board games, booksbr- Walk-in closets, jetted tub, ceiling fansbrbrGENERALbr- Free WiFibr- Central air conditioning & heatingbr- Washer & dryer, laundry detergentbr- Linens & towels, hangers, iron/boardbr- Complimentary toiletries, hair dryerbr- Keyless entrybrbrFAQbr- 3 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Stairs required to access, 3-story homebr- No bedrooms or full bathrooms on 1st floorbrbrPARKINGbr- Driveway (9 vehicles)br- RV/trailer parking available on-sitebrbr-- THE LOCATION --brbr- Walkable to public lake, beach, boat ramp, park & shopping centerbr- 2 miles to Broadneck Parkbr- 4 miles to Sandy Point State Park & Baltimore Harbor Lighthousebr- 7 miles to downtown Annapolis: historic landmarks, restaurants, shops, live entertainmentbr- 21 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/ $50 fee (+ fees & taxes, 2 max)br- No events, parties, or large gatheringsbr- Must be at least 22 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 3-story property requires exterior stairs to enter. Interior stairs are required to access all bedrooms and full bathrooms on the upper levelsbr- Your safety matters. This property features 3 exterior security cameras. Camera 1 is a Ring doorbell camera located next to the front door facing the front entrance area, camera 2 is located over the back door facing the back entrance, and camera 3 is located over the basement door facing the basement entrance. The cameras are outward facing and do not look into interior spaces. The cameras record video and audio continuously

4

Bed

3

Bath

8

Sleeps

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