
Vacation rentals with outdoor seating in Annapolis
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Annapolis
Guests agree: these outdoor seating rentals 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.

Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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.

Historic 3 Bedroom Downtown Annapolis Townhome
Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, Downtown Restaurants, Bars, Shopping, and Festivals. Enjoy and relax on your large private, fenced-in patio or in your modern living room. While the restaurant scene is mouth-watering in Annapolis, you can also stay "home" and cook in your gourmet kitchen. Explore all that Annapolis has to offer from the comfort of your home away from home! No on-site parking but lots of off.

Waterfront Chesapeake Bay Sunrises & Fishing Pier!
Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Funky Uptown Apt meets Downtown - Hist District
Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen, BR2 with Full. LR w/sofa

Stay aboard the S/V MY STUDIO on Annapolis Harbor
Discover life aboard a comfortably equipped sailing yacht. Great for couples on a weekend getaway, and child friendly for families looking to include their little pirates. Hands down this is a wonderful way to visit Historic Annapolis and Naval Academy. We love the opportunity to share our boat, and help create a memorable vacation. Weather permitting, Private Sailing Cruises can be arranged during your stay for an additional charge. Cheers, and I look forward to welcoming you aboard.

Chesapeake Comfort, Annapolis.
Veteran Superhost! Annapolis Bungalow Home. Professionally cleaned and a full time Airbnb. I have been a Superhost with my listings for over 10 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch. Queen Bedroom on ground floor. 2nd Queen Bedroom on lower level w/bathroom. Loft bedroom has 2 full size beds.

Annapolis Waterfront Condo - Unit #: A-203
Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

Summer on the Bay | Near USNA | Private Retreat
Wake up minutes from the Chesapeake Bay and unwind in a peaceful, private retreat just 4 miles from Historic Annapolis and the Naval Academy. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtful interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, couples romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

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!

Weems Creek Cottage, Annapolis Waterfront
(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.
Popular amenities for Annapolis outdoor seating rentals
House rentals with outdoor seating

4 bedrooms, 7 beds, 3 bath completely updated

Charming house; walk to everywhere in Annapolis

Sophisticated & Spacious Historic Home w/ Parking!

Fleet St Retreat in Downtown - Great Location!

Annapolis Cottage at Bay Ridge, Renovated

Kent Island Waterfront Home with Amazing Sunsets

Luxury Modern Home on Water+Hotub- Annapolis 25min

Serene Riverfront Home
Apartment rentals with outdoor seating

Blue Crab Lodge

Celebrate Summer In Your Private Pool & Hot Tub

A unique place on sue creek

Charming 18th C. Apt in DTA

Cozy Waterfront Apartment Chester, MD

Charming Studio in the heart of St. Michael's, MD.

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

Just Like Home - Private Entrance Apt in DMV Area
Condo rentals with outdoor seating

Lovely 1BR condo in quiet neighborhood

Modern, spotless 1br for families or work

New Downtown Annapolis Condo With Free Parking

Modern Condo, 2 Bed/2 Bath, Rooftop - 6 PPL

Attractive one-bedroom unit on Capitol Hill

Capitol Hill 2-BD/1.5-BA - Prime location!

Sunny Apartment in Historic Capitol Hill

DC’s Southwest and Navy Yard Welcomes You!
When is the best time to visit Annapolis?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,047 | ﺩ.ﺇ933 | ﺩ.ﺇ973 | ﺩ.ﺇ1,087 | ﺩ.ﺇ1,326 | ﺩ.ﺇ1,219 | ﺩ.ﺇ1,098 | ﺩ.ﺇ1,208 | ﺩ.ﺇ1,267 | ﺩ.ﺇ1,414 | ﺩ.ﺇ1,208 | ﺩ.ﺇ1,194 |
| 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 |
Quick stats about vacation rentals with outdoor seating in Annapolis

Total vacation rentals
Explore 310 vacation rentals in Annapolis

Nightly prices starting at
Annapolis vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

Verified guest reviews
Over 16,440 verified reviews to help you choose

Family-friendly vacation rentals
250 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wi-Fi availability
310 of Annapolis vacation 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!
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- Georgetown University
- Walter E Washington Convention Center
- National Mall
- M&T Bank Stadium
- Nationals Park
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Baltimore Convention Center
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
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- Patterson Park
- National Harbor
- Smithsonian American Art Museum
- Great Falls Park
- Six Flags America
- Johns Hopkins University




