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Annapolis, MD short term rentals
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Best Short term and Weekly rentals in Annapolis, MD

Discover Short-Term Rentals by the Sea in Annapolis, MD

Experience relaxing maritime vibes at coastal short-term rentals in Annapolis, MD, situated short distances from regional beach-town boardwalks.

Historic Renovated Home In The Heart Of Downtown - Annapolis, MD
10 192 reviews

Historic Renovated Home In The Heart Of Downtown

apartment, Annapolis
This East Street home in downtown Annapolis offers a prime location, two blocks from the U.S. Naval Academy, City Dock, and the Annapolis Yacht Club.
This 2400-square-foot house features four bedrooms, two bathrooms, and accommodates eight guests, boasting a private backyard, screened porch, designer furnishings, and a fully equipped kitchen including a dishwasher.

Check Out 5-Star Lodgings in Annapolis, MD

Experience the pinnacle of comfort in Annapolis, MD with a luxury rental designed to meet your every need.

Charming 5br Naptown Home <1 Mile To Stadium - Annapolis, MD
10 78 reviews

Charming 5br Naptown Home <1 Mile To Stadium

apartment, Annapolis
This family-friendly vacation home is located in Annapolis, within walking distance of People's Brewer Hill Cemetery, Helen Avalynne Tawes Garden, and Maryland Hall for Creative Arts, and a short drive from the US Naval Academy. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 4-bedroom home offers ample space for up to 14 guests and features a fully equipped kitchen, a fireplace, a fenced private yard, and a tennis court, making it perfect for families and groups seeking a comfortable and enjoyable stay.

Frequently Asked Questions about short term rentals in Annapolis, MD

  • Which top landmarks you shouldn't miss in Annapolis, MD?

    Annapolis is full of historic charm! You definitely want to check out the Maryland State House, the United States Naval Academy, and the historic Annapolis City Dock. You can even take a boat tour to see the city from the water!
  • What are the best short term rentals in Annapolis, MD?

  • What kind of weather can travelers expect in Annapolis, MD?

    Annapolis has four distinct seasons. Summers are hot and humid, with average temperatures in the 80s. Winters are mild, with average temperatures in the 40s. Spring and fall are beautiful, with mild temperatures and plenty of sunshine. Don't forget to pack accordingly!
  • What are the best short term rentals with a pool in Annapolis, MD?

  • Are there any famous stadiums or sports arenas in Annapolis, MD?

    Annapolis doesn't have any major league stadiums or arenas. But, if you're a sports fan, you can check out the Navy-Marine Corps Memorial Stadium, home to the US Naval Academy's football team. It's a great place to catch a game and experience some college football spirit!
  • What are the best short term rentals with a jacuzzi in Annapolis, MD?

    The best short term rentals with a jacuzzi in Annapolis, MD are Downtown Annapolis Condo W/ Free Parking + Coffee, Bay View Studio Apartment and Eastport Bungalow.

  • What notable natural landmarks are near Annapolis, MD?

    Just a short drive from Annapolis, you'll find the beautiful Chesapeake Bay. You can enjoy a day of fishing, kayaking, or just relaxing on the beach. If you're looking for something a little more adventurous, check out the hiking trails at Quiet Waters Park.
  • What are the best short term rentals for families and kids in Annapolis, MD?

    The best short term rentals for families and kids in Annapolis, MD are South River Park Apartment, 2a One Bedroom Annapolis Apartment and Relaxing Water Views - Mill Creek Cottage.

  • What part of Annapolis, MD is ideal for finding lodging?

    The downtown area of Annapolis is a great place to stay, with plenty of hotels, bed and breakfasts, and vacation rentals. You'll be within walking distance of all the main attractions and restaurants. If you're looking for something a little more secluded, you can check out the neighborhoods near the Chesapeake Bay.

Popular destinations

Search Family Short-Term Rentals in Annapolis, MD

Family trips to Annapolis, MD thrive in rentals that provide easy beach access and plenty of room to spread out.

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard - Annapolis, MD
10 22 reviews

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard

apartment, Annapolis
This Annapolis vacation rental, located in the Admiral Heights neighborhood, is 0.7 miles from the Navy-Marine Corps Memorial Stadium and 2 miles from both downtown Annapolis and the U.S. Naval Academy.
This four-bedroom, two-bathroom home sleeps nine guests and features a private backyard with a fire pit, a fully equipped kitchen with stainless steel appliances, high-speed WiFi, Smart TVs, and driveway parking; nearby attractions include the Smithsonian Environmental Research Center and Peters Cove.
Pet Friendly | Park Free & Walk To Usna Stadium - Annapolis, MD
10 66 reviews

Pet Friendly | Park Free & Walk To Usna Stadium

apartment, Annapolis
This 4-bedroom house is located in West Annapolis, just a short walk from the Navy-Marine Corps Stadium and a variety of restaurants, shops, and the new RAR Brewery. This accommodation has excellent user, location, and cleanliness ratings.
The house has two bathrooms and can accommodate up to 10 guests. Amenities include a private bar and gym in the garage, a fenced-in backyard, a full kitchen, and Apple TV.
Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
No reviews

Chapel Gate 3br Steps To City Dock & Naval Academy

apartment, Annapolis
This pet-friendly, three-bedroom apartment offers 1190 square feet of living space in Annapolis's Historic District, located just outside Gate 3 of the U.S. Naval Academy and a short walk to City Dock.
This top-floor, two-level rental accommodates up to six guests and features a fully equipped kitchen, in-unit laundry, a Roku TV, and a terrace, with outdoor grilling and patio access available.
Private Annapolis Suite | Dogs Welcome + Parking - Annapolis, MD
10 16 reviews

Private Annapolis Suite | Dogs Welcome + Parking

B&B, Arnold
Tide and Timber Retreat, a dog-friendly guesthouse in Arnold, Maryland, is conveniently located 5 miles from the Navy-Marine Corps Memorial Stadium and 6 miles from downtown Annapolis.
This private basement apartment sleeps four, features a full kitchen with dishwasher, in-unit laundry, a dedicated parking spot, access to a shared yard with a children's play area and firepit, and offers flexible check-in/check-out times.

Neighborhoods and points of interest in Annapolis, MD

Top Dog-Friendly Lodgings in Annapolis, MD

Forget the post-beach mess; these short-term rentals in Annapolis, MD feature dog-friendly amenities.

Downtown Annapolis King George 3rd Floor Hideaway - Annapolis, MD
9.8 153 reviews

Downtown Annapolis King George 3rd Floor Hideaway

apartment, Annapolis
This apartment is located in Downtown Annapolis, just a short walk from the Annapolis Harbor and 30 miles from Baltimore. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment features one bedroom and one bathroom, offering 700 square feet of living space. You'll enjoy a fully equipped kitchen, a private terrace, and a garden with barbecue facilities, perfect for relaxing after a day exploring Annapolis.

Best Annapolis, MD lodging with a balcony

Acrross From Usna Gate 3 W Patio At Hanover House - Annapolis, MD
9.9 75 reviews

Acrross From Usna Gate 3 W Patio At Hanover House

apartment, Annapolis
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 30 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
Liberty Lookout - Annapolis, MD
No reviews

Liberty Lookout

apartment, Annapolis
Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium - Annapolis, MD
9.2 20 reviews

Cute And Close To Downtown! Off Street Parking W/ Short Walk To Academy/stadium

apartment, Annapolis

Best Annapolis, MD lodging with a kitchen

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park - Annapolis, MD
9.5 11 reviews

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

apartment, Annapolis
Walk To Navy Stadium Private Studio W Parking - Annapolis, MD
10 1 review

Walk To Navy Stadium Private Studio W Parking

studio, Annapolis
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
10 21 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis
Upscale Family Retreat Near Downtown Annapolis W Resort-style Outdoor Spaces - Annapolis, MD
10 4 reviews

Upscale Family Retreat Near Downtown Annapolis W Resort-style Outdoor Spaces

apartment, Annapolis

Best Annapolis, MD lodging with laundry available

Charming Historic Annapolis Home With Two Off-street Parking Places! - Annapolis, MD
10 215 reviews

Charming Historic Annapolis Home With Two Off-street Parking Places!

apartment, Annapolis
Historic Charm | Steps From City Dock And The Yard - Annapolis, MD
9.9 47 reviews

Historic Charm | Steps From City Dock And The Yard

apartment, Annapolis
Ahoy! Game Room, Screened Porch, Yard Mins To Dta - Annapolis, MD
9.8 18 reviews

Ahoy! Game Room, Screened Porch, Yard Mins To Dta

apartment, Annapolis
Annapolis Charm Bright 3br In Downtown - Annapolis, MD
9.6 28 reviews

Annapolis Charm Bright 3br In Downtown

apartment, Annapolis
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