Vacation Home Rentals By Owner In Annapolis, MD

$364.2

8 Bells Bungalow - Cozy, Stylish, Prime Location

Annapolis, Maryland, United States

Stylish and comfortable home in Admiral Heights, just minutes from downtown Annapolis, the waterfront & vibrant dining/shopping. Relax in a quiet neighborhood with easy access to Navy-Marine Corps Memorial Stadium, U.S. Naval Academy, downtown, and the Annapolis Arts District on West Street — perfect for game days, sightseeing, or weekend getaways. Walk or drive to local favorites, enjoy central convenience, and explore historic Annapolis & Chesapeake Bay experiences

3

Bed

2

Bath

6

Sleeps

$473.67

/ Nightly

Private Vacation Home

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis, Maryland, United States

Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Naval Academy, Downtown Annapolis and Historic Maryland Ave, this 1875 home has been fully renovated and updated for our guests. Boasting beautiful views of Historic Paca House and book ended by Spa Creek and St. John's College, the location is amazing.brKid friendly house with a quiet and secluded back patio for relaxing.brEntire interior (baths, kitchen, flooring and furnishing) was just renovated this year. Hotel quality linens and towels ready for your next trip to Downtown Annapolis.br

3

Bed

2

Bath

8

Sleeps

$641.25

/ Nightly

Private Vacation Home

Modern Retreat w/ Fire Pit & Parking

Annapolis, Maryland, United States

Immerse yourself in the best that Annapolis has to offer while staying in this completely renovated, modern ranch getaway. Cozy up indoors with show or movie on the smart TVs or outdoors at the fire pit with Adirondack seating for six. Unwind and relax in any of four finely appointed, luxurious king bedrooms. The yard is partially fenced for privacy within a quiet neighborhood. The location is ideal with easy access to Navy Stadium and the Naval Academy, downtown Annapolis, Parole, and Anne Arundel Medical Center.

Bed

Bath

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$570

/ Nightly

Private Vacation Home

Game Days & Family Stays at Dog-Friendly Home Near Navy Stadium w Private Fenced-In Yard

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrA new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect blend of comfort and convenience at this professionally updated, family-friendly home nestled in a peaceful cul de sac with a driveway. Located just a few blocks from the Navy-Marine Corps Memorial Stadium and minutes from the quaint shops of West Annapolis and the historic charm of downtown, this home offers an unforgettable stay. brbr brbrProperty Highlights brbrSpacious & Stylish: Recently redecorated with fresh, modern decor brbrOutdoor Oasis: Enjoy the private backyard with a cozy fire pit—perfect for family gatherings. brbrFully Equipped Kitchen: Cook meals effortlessly with stainless steel appliances. brbrAmple Gathering Spaces: Multiple levels offer room to relax and unwind. brbrPrime Location: Walkable to stadium, shops, and downtown, with easy access to Baltimore, DC, and local landmarks. brbr brbrSleeping Arrangements (4 BR / 2 BA | Sleeps 9) brbrMain Floor Suite: Queen bed, ensuite bath, and Smart TV brbr2nd Floor Navy King Guestroom: King bed, shared hall bath brbr2nd Floor Peach King Guestroom: King bed, shared hall bath brbr2nd Floor Full Guestroom: Full bed with twin trundle, shared hall bath brbr brbrAmenities brbrFully-stocked kitchen with stainless steel appliances brbrHigh-speed WiFi and multiple Smart TVs for entertainment. brbrWasher and dryer for your convenience brbrLuxury linens, boutique-level service, and a complimentary starter pack of toiletries and essentials brbrDriveway parking for multiple vehicles brbrDog-Friendly: Bring your furry friend for a $150 non-refundable pet fee per pet. brbr brbrLocation at a Glance brbrNavy-Marine Corps Memorial Stadium: 0.7 miles brbrU.S. Naval Academy: 2 miles brbrDowntown Annapolis: 2 miles brbrWashington, DC: 30 miles brbrBaltimore: 30 miles brbr brbrHouse Rules brbrGuests must be 25+ to book. brbrNo parties, smoking, or events allowed. brbrQuiet hours are enforced—please respect our neighbors. brbrCheck-in: 4:00 PM | Check-out: 11:00 AM brbr brbrWhether you're here to cheer at the Navy Stadium, explore the cobblestone streets of Annapolis, or relax with loved ones, this home offers the perfect setting for creating lasting memories.

4

Bed

2

Bath

9

Sleeps

$444.55

/ Nightly

Private Vacation Home

Spacious 4-bedroom house with AC in brilliant Annapolis

Annapolis, Maryland, United States

Unwind in Annapolis at this pleasant house perfect for groups or families. With four bedrooms, including three queen beds, guests find plenty of space to relax. The single bathroom features both a bathtub and shower, making it easy to refresh after a day of exploring. Stay comfortable year-round with heating and AC, and enjoy the convenience of an iron and hair dryer. Whether you’re lounging indoors or getting ready for a night out, this tranquil home offers a nice balance of comfort and ease. You’re sure to make fantastic memories with a stay at our place.

4

Bed

1

Bath

6

Sleeps

$505.4

/ Nightly

Private Vacation Home

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Annapolis, Maryland, United States

Discover the beauty of Annapolis from this fantastic 5-bedroom house. With two queen beds and a peaceful bathroom featuring a bathtub and hair dryer, guests find comfort and convenience throughout their stay. The lovely space is perfect for families or groups looking to unwind and enjoy quality time together. Kick back, relax, and enjoy everything Annapolis and our house has to offer.

Bed

Bath

Sleeps

$698.25

/ Nightly

Private Vacation Home

MODERN 2022 NEWLY BUILT TOWNHOME

Annapolis, Maryland, United States

Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two living areas with a separate dining room, screened in porch and backyard. Each bedroom offers an en-suite bathroom, and you could not be more centrally-located to all that Eastport has to offer - step outside to famous Boatyard Bar & Grill and Forward Brewing directly across the street. Convenient street parking out front - walk to downtown Annapolis and USNA.brThe spacebrWhere you will sleep:brMaster bedroom - King Bedroom Suite with two walk-in closets, upscale and modern en-suite bathroom with oversized shower featuring rain shower and multiple jets, towel warmer for that extra touch.brbrFront bedroom - King Bedroom Suite with office desk/chair for workspace. En-suite bath with full tub.brbrMiddle bedroom - Queen Bedroom Suite with en-suite bathroom.brbrAll bedrooms upstairs. Washer and Dryer in hallway closet space upstairs. All amenities are top-line and well stocked.brbrMain level features a front living room with queen sleeper sofa, dual-sided gas fireplace that opens to an 8-person dining room on the other side. Open concept Chef's kitchen with waterfall island and seating for four - two beverage fridges for entertaining. Cozy living room with oversized sectional that leads to a backyard screened in porch with private backyard.brGuest accessbrEntire townhousebrOther things to notebrWe want you to feel that every detail has been thought of and that you can walk in, relax and enjoy with friends. This open concept floor plan allows for both comfort and ease and is the perfect location for walking to all that Eastport and Annapolis have to offer.

Bed

Bath

Sleeps

$641.48

/ Nightly

Private Vacation Home

***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.

Annapolis, Maryland, United States

1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in downtown's Arts District, we are conveniently located in walking distance to City Dock, USNA, Navy Stadium, or to the many restaurants and shops Annapolis has to offer. Private driveway so parking is never a problem. Great fenced in backyard and patio for entertaining! 3 bedroom, 2.5 bath, with additional sleeping options in the finished basement (queen murphy bed) and a pull out sofa in the living room (queen). This home checks all the boxes for a memorable stay in Annapolis.brbrSorry, we are already booked for '22, '23, & '24 Commissioning Weeks.

Bed

Bath

Sleeps

$841.25

/ Nightly

Private Vacation Home

Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown

Annapolis, Maryland, United States

This clean, peaceful, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect for families or small groups, like book clubs or reunions!brBEDROOMS: 5 BRs w 4 queens and 1 full-over-full bunk bed sleep up to 10 guests. Denver Mattress Company mattresses & soft Supima cotton sheets comfort you, every night. BR 1 & BR 2 have private BAs. BR 1, BR 2 & BR 3 have private sliding doors leading onto the lower deck with its water front view. BR 4 (full-over-full bunk bed) & BR 5 (queen bed) front a quiet, single lane road.brATTRACTIONS: 15-min drive to Naval Academy & downtown Annapolis. 8-min drive to Quiet Waters Park. 5-min drive to a Giant grocery, Starbucks, restaurants & a pharmacy. 5-min walk to historic Highland Beach & the Chesapeake Bay.brDINING AREA: Perfect for cooking & eating together! Dining table with 8 chairs and 4 bar stools nearby at the counter. Deck chairs & a foldable table make deck meals a convenient option.brKITCHEN: Top floor, NUT-FREE, well-stocked, well-equipped kitchen has plenty of chef’s items in the pantry, new electric range & granite countertops. The sink has an Instant Hot and an under-the-sink reverse osmosis water system. The Bosch dishwasher is so quiet that you’ll barely hear it cleaning for you.brTOP FLOOR: Open floor design to maximize waterfront view. Regulation-size ping pong table, TV, games & puzzles are available. Top floor has a bright, gourmet kitchen, full BA & home office/fitness room. Half-covered upper deck for outdoor relaxation.brNEIGHBORHOOD: Scenic, low-traffic street popular with joggers. 5-min walk to Chesapeake Bay & to the historic Highland Beach community. brVIEW: 100-ft waterfront view with a Living Shoreline and a wildlife critical area. Turtles or ducks may visit at high tide. Hummingbirds, butterflies & more may visit the pollinator-friendly garden. Either deck or large backyard are ideal for family games, meditation, yoga or tai chi. Postcard sunset! No pier.brWATER: All household water arrives filtered and drinkable from the well. The kitchen has an under-the-sink reverse osmosis system and an Instant Hot. brWIFI: Free to our guests & provided by Verizon.brEXTRAS: hair dryer, iron & ironing board, deck chairs & garage use. Generous driveway & street parking accommodate 5 cars.brNOTE: Due to a child's allergy, this is a NUT-FREE VACATION HOUSE. Do not bring nuts inside, please.

Bed

Bath

Sleeps

$367.02

/ Nightly

Private Vacation Home

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Annapolis, Maryland, United States

The Corner House – Quaint and Cozy 2 Bedroom Suite with ParkingbrThe Corner House is a hidden gem located in the quaint President’s Hill neighborhood in historic Annapolis. New to the market, this suite is a cozy nook nestled on the third floor of this historic house. It is one block from West Street. This area of Annapolis is a vibrant and historically significant area that offers a mix of history, arts, culture, dining, and entertainment, making it a unique and lively part of the city.brbrSituated just a short walk from the heart of the West Street Arts District, The Corner House is a home away from home. Enter through a white picket fence and onto a covered front porch. This is where you can enjoy your morning coffee and your afternoon tea or glass of wine when you return from your ventures. Enjoy the artwork of local and east coast regional artists that is displayed in the foyer and throughout the home.br brKnown as “Cunningham’s Retreat”, this loft-style suite boasts both a nautical character and coastal charm. One of three suites in this tri-gabled opulent Hill Street home offers a tranquil and comfortable vacation experience. This beautifully designed and decorated haven has two bedrooms, one bathroom and a kitchen. Includes off street parking for one vehicle. brbrMoreover, guests will enjoy easy access to a vibrant scene with nearby restaurants, taverns, galleries, and music venues. This location is conveniently situated. It has easy walking equidistance to everything uptown and downtown Annapolis, such as Maryland State House, Governor’s Mansion, Market House, Ego Alley, St John’s College, US Naval Academy, Navy-Maine Corps Memorial Stadium, historic sites, waterfront locations, and parks.brbrWest Street in historic downtown Annapolis holds significant cultural and historical importance. It is renowned for its thriving arts and culture scene. It’s home to numerous art galleries, studios, and performance venues, making it a focal point for visitors, artists, and art enthusiasts. While known for its artistic vibe, West Street also retains its historical charm with well-preserved architecture, including charming row houses and historic buildings. The street offers a diverse range of dining options, from trendy cafes to upscale restaurants. It’s also a hub for live music, with bars and venues hosting local musicians and bands. West Street features boutique and specialty shops making it a great destination for shopping for unique and artisanal items.brbrThroughout the year, West Street hosts various festivals and events, including art festivals, live music performances, and cultural celebrations fostering community and unity.brbrGuests will enjoy their quiet and serene visit at The Corner House. This is a legally licensed rental property. We strongly enforce our policies of no parties and no illicit drug use. This is a non-smoking property. Pets are not permitted. No children under the age of 12 years old.br

Bed

Bath

Sleeps

$785.71

/ Nightly

Private Vacation Home

Bay Home in Annapolis with Private Dock

Annapolis, Maryland, United States

Complement your next outing to the Annapolis area with a stay at our beautiful waterfront home primely situated on the Chesapeake Bay! Featuring a well-equipped modern kitchen, deck with outdoor dining area, separate comfortable outdoor seating area, an outdoor fire pit, and dock with 4 adirondack chairs to enjoy the sunsets with a beverage of your choice. Stroll through Sandy Point State park and visit the Colonial Annapolis Historic District and the Annapolis Maritime Museum.brbrOur Bay Home has three bedrooms, a large kitchen with island and dining, two living areas, wood burning fire place, multiple outdoor areas, an outdoor fire pit, and dock. brbrThe upper level bedrom is the largest with its own bathroom complete with soaking tub and seperate shower, double sinks and closet area. The large capacity washer and dryer are in the closet area. Off the principle bedroom is your private deck with 2 loungers and a beautiful view of the bay. You might even see a bald eagle or osprey looking for their next fish to catch. brbrThe other two bedrooms are located on the main level and share a full bathroom. The Queen Bedroom has a four poster bed, TV, closet, and french doors with a view of the bay. The double-bunk-bed room has a large closet and shelves. Both bedrooms have blackout blinds. brbrAt the end of the hall is a large TV/Exercise/Game room. There is an 85` TV, cozy couch and lounge chair to relax in or close the door and have the kids hang out in there while the adults are in the main area of the home. There are games, a pelaton, rowing machine, hand weights, yoga mats and a ping pong table. brbrThe kitchen-living-dining area share the same space. There is a large L-shaped island with a five burner gas stove with oven, a microwave, prep and serve areas, bar stools and book shelves with our favorite cookbooks. There is a hand powered Italian meat slicer for the adventurous charcuterie maker. The large velvet couch with big pillows is a great place to enjoy the fire place and watch the weather and birds outside. The dining table has four chairs and the bar has four bar stools. brOut the door to the right side of the kitchen is a the grilling area with a ceramic charcoal grill. It takes about thirty minutes to warm up and then its ready to grill all your favorite foods. To the back of the house is a large deck going the full width of the house with a large outdoor couch and chairs, and a 10 person dining table and pizza oven. brbrTo the left of the house is a screened in porch area with a fan, two chairs and a cafe table. We like to go out there and watch the rain storms come in and go by. brbrIn the back yard, is a fire pit with seating for six people and a huge Sycamore tree. Its a great space for playing bocci ball. The dock is one of our favorite place to enjoy coffee while watching the sun come up and a different beverage for watching the magnificent sunsets. The four adorondack chairs make this time quiet comfortable. Fishing from the dock can be quite promising as well!brbrThe front yard is long and flat with the driveway flanking the one side. There is a large garden on the other side with many Crape Myrtle trees. The driveway leads to the round parking area in front of the house. br brWe are located about 15 minutes from downtown Annapolis in a quiet, one street, neighborhood with tons of large trees and wildlife sightings daily.brbrWe are 15 minutes from most places around Annapolis and so a car is the best option for accessing our property.brbrFor general questions: please contact Joel and for emergencies contact Evelyn.brbrOur home is located in a `one street` neighborhood with wonderful neighbors walking their dogs daily.

Bed

Bath

Sleeps

$952.86

/ Nightly

Private Vacation Home

Steps to Downtown Annapolis & Spa Creek from Stunning Craftsman with Game Room, Parking and Backyard

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWalk to Everything Ideal for Families & Groups brbr brbrWelcome to your Eastport escape! Stay in this stunning, professionally decorated Craftsman-style home just steps from the waterfront and all the shops, restaurants, and charm of downtown Annapolis. With three levels of beautifully appointed living space, this 4-bedroom, 3.5-bath home offers everything you need for a relaxing weekend getaway or an extended stay with family and friends. brbr brbrHighlights brbrFully-equipped Gourmet Kitchen with modern appliances, ample counter space, and seating for everyone: brbrDining table seats 10 brbrKitchen table seats 5 brbrBreakfast bar seats 4 brbr brbrMultiple Gathering Areas: brbrMain living room with gas fireplace & flatscreen TV brbrLower-level rec room with 85 TV, bar seating, gas fireplace, arcade machine, foosball, board games, and Queen pull-out sofa brbrCozy backyard with furnished deck, grill, and Solo Stove fire pit brbr brbrOutdoor Spaces: brbrCovered front porch brbrPrivate balcony off King Suite, perfect for sipping your morning coffee brbrFully-fenced yard with Adirondack chairs, dining table, with outdoor games and yard toys brbr brbrSleeping Arrangements (Sleeps 12): brbrKing Suite (2nd Floor) brbrKing bed, Private balcony, Flatscreen TV & electric fireplace brbrWalk-in closet brbrSpa-like ensuite with dual vanity, soaking tub & custom shower brbr brbrQueen Bedroom (2nd Floor) brbrQueen bed + Twin trundle brbrDesk brbrShares buddy bath with Bunk Room brbr brbrBunk Room (2nd Floor) brbrTwin over Queen bunk brbrShares buddy bath brbr brbrQueen Bedroom (Lower Level) brbrQueen bed brbrAdjacent full hall bath brbr brbrRec Room (Lower Level) brbrQueen sleeper sofa, Full bath access brbr brbrEntertainment, Comfort & Work Stations: brbr3 Smart TVs | Strong WiFi throughout brbr3 Gas fireplaces brbrWood-burning Solo Stove in backyard (BYO firewood & s’mores supplies) brbrArcade machine, foosball table, and board games for family fun brbrFast WiFi throughout the house, with cheerful work area in lower-level den and a desk in one of the upstairs bedrooms brbrWasher & dryer in-home brbrAll bedrooms have individual charging stations brbrProfessionally laundered linens and bath towels provided brbrStarter pack of toiletries & household essentials included brbrA portable crib and booster seat are also available for your littlest guests. brbr brbrWalkable to: brbrDavis Park Dock – 0.1 mi brbrEastport restaurants & shops – 0.2 mi brbrDowntown Annapolis – 0.7 mi brbrU.S. Naval Academy – 0.9 mi brbrEasy access to Washington, DC (30 mi) and Baltimore (25 mi) brbr brbrHouse Rules: brbrNo pets, parties, or smoking brbrPrimary renter must be 25+ and present during stay brbrExterior doorbell camera & legal decibel monitor for safety brbrOther things to note brbrPlease note that we may collect additional information from you after confirming your booking (usually an email address) in order to comply with local regulations and to provide the best possible experience. brbr brbrThis home is the perfect blend of luxurious comfort and unbeatable location. Whether you’re planning a weekend filled with waterfront adventures, a midweek work-from-home escape, or a festive family gathering, you’ll love calling this Eastport gem your home base in Annapolis.

Bed

Bath

Sleeps

$934.8

/ Nightly

Private Vacation Home

Winter Retreat Near Naval Academy+ Hot Tub!

Annapolis, Maryland, United States

◉ 5-min stroll to private beach br◉ Dock access for your boat br◉ Gourmet kitchen + private chef (by request) br◉ Stunning bay views from kitchen & bedrooms br◉ Ensuite baths in every bedroom br◉ 15 min to Naval Academy & Old Town br◉ 2 min to Starbucks & Giant br◉ Hot tub w/ water views br◉ Adirondack chairs & rocking chairs w/water viewsbr◉ Charcoal & propane grill br◉ Huge deck for sunbathing & lounging

Bed

Bath

Sleeps

$942.75

/ Nightly

Private Vacation Home

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis, Maryland, United States

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay! Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings! High end furniture! Hotel Luxury Mattresses! TV's in every bedroom! High Speed Internet!

4

Bed

2

Bath

12

Sleeps

$427.5

/ Nightly

Private Vacation Home

DTA 2 bdrm w/parking, pet friendly, great location with all of the amenities!

Annapolis, Maryland, United States

This 2-bedroom non-investor house has everything you need for a great stay! We live there part time so it’s not an empty rental. Great kitchen, outdoor space, parking and location! Pet friendly with a doggy door and fully fenced yard. It’s a 3 bdrm house and we lock the primary suite for our 2 bdrm rentals. (The 3 bdrm is a separate listing). You have the house to yourself either: way-no sharing with owners or other renters. Amenities include a gas fireplace, dual zoned heat/ac, chimnea and wood, most streaming services, cotton linens and super comfy (practically new) beds to name a few features.brbrIf you want to cook for you mid this is the house for you. A substantial Napoleon grill (propane and back up provided along with every grill accessory you could want), double gas oven, every spice, herb condiment and utensil you could need. This is a fully appointed kitchen as we live there part time. When was the last time you went to a rental and had nice knives A cheese grater A rolling pin Saran wrap and aluminum foil It's all here. The open floor plan seats 14 for dinner: 8 dining chairs and 6 barstools!

Bed

Bath

Sleeps

$300.69

/ Nightly

Private Vacation Home

1 Block to USNA Stadium: Modern Annapolis Home!

Annapolis, Maryland, United States

Central Location | New Build | In-Unit Laundry | Fire Pit | 2 Mi to USNAbrbrSettle into this Annapolis vacation rental that suits both work and play. Just 2 miles from downtown, the State House, and the Naval Academy — and less than a half-mile from Navy-Marine Corps Memorial Stadium — this 2-bedroom, 1-bath home makes every trip easy. After a day of meetings, sightseeing, or game-day excitement, fire up the grill or gather around the fire pit to relax.brbr-- THE PROPERTY --brbrRENT-002085-2025brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 queen sleeper sofabrbrMAIN FEATURESbr- Wood-burning fire pitbr- Gas grillbr- TVsbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig (coffee provided), microwavebr- Dishware/flatware, trash bags/paper towelsbr- Island w/ seatingbrbrGENERALbr- Free WiFibr- Central A/C & heat, ceiling fansbr- Washer/dryer, hangersbr- Linens/towels, hair dryerbrbrFAQbr- 1 exterior security camera (facing driveway)brbrACCESSIBILITYbr- Single-story home, 2 exterior staircases to enterbrbrPARKINGbr- Driveway (2 vehicles)br- Garage not availablebrbr-- THE LOCATION --brbr- 1 block to Navy-Marine Corps Memorial Stadiumbr- 2 miles to Downtown Annapolis, Annapolis City Dockbr- 2 miles to Maryland State Housebr- 2 miles to United States Naval Academybr- 22 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- 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 2 exterior staircases to enterbr- Your safety matters. This property features 1 exterior security camera on the home facing the driveway. The camera does not look into any interior spaces. It records video and sound when activated by motionbr- The garage is not available for guest use

Bed

Bath

Sleeps

$503.17

/ Nightly

Private Vacation Home

Eastport 3 bedroom Cottage: Walk to Downtown

Annapolis, Maryland, United States

Summary:brbrDiscover Annapolis from our charming Eastport cottage! This updated home comfortably sleeps 8 and is perfect for USNA events or a relaxing getaway. Enjoy a fully equipped kitchen, spacious backyard and a prime location just a 15-minute walk from Downtown Annapolis. Experience the best of historic Eastport with its marinas, waterfront dining, and local shops right at your doorstep. Your ideal family or group retreat awaits!brbrbrbrThe Space:brbrWelcome to our charming and updated cottage home, your perfect base for exploring all that Annapolis has to offer! Nestled in the historic Eastport neighborhood, this home is ideal for families and friends.brbrbrbrStep inside and you'll be greeted by a bright, inviting living area filled with ample natural light. The home offers several comfortable spaces to unwind, including a sun-filled sitting room and an additional living area on the lower level.brbrbrbrKey Features:brbr Fully equipped kitchen with modern stainless steel appliances and a breakfast bar.brbr Adjacent dining area for enjoying home-cooked meals.brbr Two full bathrooms with contemporary fixtures and complimentary toiletries.brbr Spacious and private backyard area, ideal for relaxing and outdoor entertaining.brbrbrbrSleeping Arrangements:brbr Master Bedroom: One plush Queen size bedbrbr Second Bedroom: One cozy Full size bedbrbrThird Bedroom: Two Double bedsbrbrbrbrGuest Access:brbrYou will have private and exclusive access to the entire home throughout your stay. This includes all interior spaces—bedrooms, bathrooms, kitchen, and living areas—as well as the private backyard. Enjoy the comfort and privacy of having the whole space to yourselves.brbrbrbrThe Neighborhood:brbrOur home is close to Eastport staples such as Vin909, Eastport Kitchen, Adam's Taphouse, Blackwall Hitch, and a short Uber Ride to Eastport Restaurant Row.brbrbrbrOther Things to Note:brbrFor your security and peace of mind, please be aware that exterior security cameras are present on the property. These cameras monitor the exterior of the home only and do not have views of any interior spaces.brbr brbrCity of Annapolis Rental License: RENT-000027-2026brbrbrbrInteraction with Guests:brbrWe respect our guests' privacy and offer a self-check-in process for your convenience. While we will not be present during your stay, we are always available via the messaging app or phone if you have any questions or need assistance.

Bed

Bath

Sleeps

$551.3

/ Nightly

Private Vacation Home

Walk to DTA & USNA | Pet-Friendly Home

Annapolis, Maryland, United States

Summary:brbrBring the whole crew — dogs included. This 3-bedroom Annapolis home is walkable to Downtown, Navy tailgates, and USNA Stadium. Inside: bright living spaces, a sunny front room, breakfast nook, and sunroom overlooking the backyard. A king suite and two queens upstairs. Outside, the fenced yard has string lights, a fire pit, BBQ grill, and corn hole — everything for a perfect evening under the stars. Full bath upstairs, half bath on the main level. Free parking and high-speed WiFibrbrbrbrThe Space:brbrBEDROOMSbrbrThree bedrooms upstairs. The primary suite has a king bed. The other two bedrooms each have queen beds. Bedroom 2 includes a desk and workspace for remote work. Fresh linens provided.brbrBATHROOMSbrbrOne full bath upstairs with the bedrooms, plus a half bath on the main level. Towels, soap, and essentials provided.brbrKITCHENbrbrFully equipped with modern appliances, cookware, dishes, utensils, and everything you need for group meals. Open layout connects to the dining room which seats 6.brbrLIVING AREASbrbrThe main floor flows from the kitchen through a large dining room into the living room. A bright sunroom overlooks the backyard — the perfect morning coffee spot. Welcoming front porch with seating. Smart TV in the living room.brbrOUTDOOR LIVINGbrbrThe fenced backyard is the highlight. String lights, fire pit, BBQ grill, corn hole, and comfortable patio seating. Everything you need for an evening outside. Pet-friendly — your dog will love the space.brbrPARKINGbrbrFree parking on the driveway and street.brbrLOCATIONbrbrWalk to Downtown Annapolis, USNA Gate 1, and Navy-Marine Corps Stadium. Close to restaurants, shops, and the waterfront. Trolley stop nearby for getting around without driving.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrPets welcome — fenced backyardbrbrFull bath upstairs, half bath on main levelbrbrbrbrGuest Access:brbrPrivate entrance. Keypad on the front doorbrbrbrbrThe Neighborhood:brbrQuiet neighborhood tucked away off West St.brbrbrbrGetting Around:brbrWalkable to downtown Annapolis and the naval stadium.brbrbrbrInteraction with Guests:brbrI follow your lead!

Bed

Bath

Sleeps

$459.61

/ Nightly

Private Vacation Home

Historic DistrictCrab Cakes and Football

Annapolis, Maryland, United States

Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock and the Navy-Marine Corps Memorial Stadium. Private parking for 2 cars!brbrThere are seven restaurants within one block including:br- Thaibr- Italianbr- Irishbr- Unique Annapolis FarebrbrThis is the perfect spot to enjoy all that Annapolis has to offer. People who know the area know that having 2 parking spots is almost unheard of. We are located in one of the most sought after neighborhoods in Annapolis. The neighborhood has a very peaceful, quiet feel. The property had once been a long term rental but we decided we'd rather share it with people coming here to vacation. We live 5-10 minutes from the property so you can enjoy your privacy but we are available if you need us. brbr

2

Bed

1

Bath

4

Sleeps

$806.14

/ Nightly

Private Vacation Home

Waterfront home in Annapolis MD with private pier

Annapolis, Maryland, United States

Waterfront home, 2000 sq feet, in Annapolis, MD on Magothy River, overlooking Chesapeake Bay, Gibson Island with private beach and pier, short drive to downtown Annapolis, Bay Bridge, Naval Academy and Kent Island, great sunset/sunrise view and good for fishing.brGreat for a wide range of occasions: couples looking for a romantic weekend away.... family reunions.... girls weekend... sailboat show etc...Special event is welcome, the driveway can park 20 cars.br3 Kayaks and 1 stand up paddle are free to use.

4

Bed

3

Bath

10

Sleeps

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