
House holiday rentals in Annapolis
Find and book unique houses on Airbnb
Quick stats about house rentals in Annapolis

Total holiday rentals
Explore 370 holiday rentals in Annapolis

Nightly prices starting at
Annapolis holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 15,530 verified reviews to help you choose

Family-friendly holiday rentals
330 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wi-Fi availability
370 of Annapolis holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Annapolis rentals

4.9 Average rating
Annapolis stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Annapolis
Guests agree: These houses are highly rated for location, cleanliness and more.

Crab Cakes and Football Historic District
Soak up the vintage charm of this restored property. The house features a private master suite balcony, an open-plan living space, chic eclectic furnishings, exposed brick, a wood burning fireplace, a front garden, and an outdoor back BBQ area. STR# 143754 When we decided to convert to a short term rental I looked at other properties in the area and how they described them. I could tell you the house was built in 1901 and is located in one of the most sought after neighborhoods in historic Annapolis. That's all well and good but to be honest there's a book on the coffee table that will tell you all the history (if you really want to know). I might not know a lot about writing a great summary but after almost 3 decades of living in Annapolis I think I know what people want: 1) Great food and drink! 2) Great location for walking to everything and.. 3) An outdoor area to enjoy the mornings and evenings during any down time. Unfortunately the one thing that can really ruin the fun is PARKING! Well guess what, we've got all the things I listed above and not one parking spot, but TWO (right at your back door!). Don't be fooled when other properties offer you a parking pass. That does not mean you'll be parking near your rental! Enjoy full access to our home. We do not live there so it is not cluttered with "stuff". Consider it a hotel with all the amenities of home! We live 5-10 minutes from the property so you'll have your privacy but we are nearby if you need assistance. We are available by text or calling for any questions or help you may need. The home is in the Art District of Annapolis right in the middle of all the fun. Enjoy the hustle and bustle of the city center during the day and evening, but return to a quiet neighborhood to recharge. Free designated parking for 2 cars. Park upon arrival and you my never need your car again until your departure! No parties. Dogs welcome on a case by case basis.

Villa Annapolitana • Parking 1 min • USNA 4 min
Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport Equipment

Elegant & Authentic Annapolis
Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

Rachel's BnB
A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

Cozy 2br home w/ parking in downtown Annapolis
Ideally located in the heart of downtown Annapolis's Historic & Art Districts. Detached home with historic charm & an inviting front porch, 1 car parking included. Open floor plan to include a living room (with queen sleeper sofa), workspace, 1/2 bath & eat in kitchen on the 1st floor. 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. A perfect location for C-Week, Boat Shows & other festivals in Historic Annapolis.

Annapolis Area Waterside Retreat
This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Country House on the Bay
My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

Fleet St Retreat in Downtown - Great Location!
We welcome you to our renovation on historic Fleet Street. Purchased in 2016 this house was taken down to the studs so everything is brand new and waiting to host you on your next trip to Annapolis. Literally a stones throw from everything downtown has to offer you can’t get closer to the action. USNA, Maryland State House, City Dock, McGarveys and Iron Rooster are just around the corner. Perfect place for two couples and a extra single. Small city patio out back.

Historic & sunny home steps from USNA/downtown
This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

Captain’s Retreat! Newly Renovated - Beach House!
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!
Popular amenities for Annapolis house rentals
House rentals with a pool

Beautiful Kent Island Getaway with Pool

Chester Riverfront At Kent Narrows

Large Home with Private Pool, Gym, Sauna, 7 Bedroo

The Little Gypsy BoHome

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

Miles Aweigh

Bay Breeze Retreat

Inground Pool | Hot Tub | Sauna | Theme Room
Weekly house rentals

Downtown Annapolis Home

Modern Annapolis Getaway - 2 Free Parking Spaces

USNA downtown house with garage parking EV 3bd/2ba

12 M to Naval Academy | Waterfront Paradise

Kent Island Waterfront Home with Amazing Sunsets

Waterfront Sanctuary only 50 Min. From DC/Balt.

3BR/2BA Annapolis Cottage

Beach Access, Hot Tub, Pet Friendly, Fully Fenced
Private house rentals

Bay Home in Annapolis with Private Dock

Welcome to Heron House! Annapolis Waterfront Oasis

Sailing Off Gloucester

Newly Renovated Downtown Charm, Game Room, Patio

Annapolis Small House in Historic District.

The Cottage at Broad Creek

Historic + Modern Home | Just Steps to Waterfront

Perfect Location! 200 steps to USNA & Downtown
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $538 NZD | $524 NZD | $513 NZD | $584 NZD | $706 NZD | $645 NZD | $569 NZD | $603 NZD | $603 NZD | $677 NZD | $567 NZD | $582 NZD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
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- M&T Bank Stadium
- Georgetown University
- National Mall
- The White House
- Walter E Washington Convention Center
- Nationals Park
- FedExField
- Baltimore Convention Center
- Johns Hopkins University
- Oriole Park at Camden Yards
- Federal Hill Park
- Arlington National Cemetery
- National Museum of African American History and Culture
- Capital One Arena
- CFG Bank Arena
- The Anthem
- Washington Monument
- Georgetown Waterfront Park
- Betterton Beach
- Howard University
- Merriweather Post Pavilion
- Smithsonian National Zoological Park
- National Harbor
- Museum of the Bible





