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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.

Walkable To Main St & Usna W Parking For 2 Cars - Annapolis, MD
10 101 reviews

Walkable To Main St & Usna W Parking For 2 Cars

apartment, Annapolis
This Annapolis vacation home is located in the heart of the historic district, just a short walk from the U.S. Naval Academy and other key landmarks. The home has received excellent ratings for location, cleanliness, and overall experience.
The 4-bedroom property comfortably sleeps 8 guests, making it ideal for families or groups of friends. Enjoy modern amenities like free Wi-Fi, a patio, a fully equipped kitchen, a garden, and a barbecue grill.

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 3-bedroom House In Annapolis Two Blocks From The Navy Stadium - Annapolis, MD
10 3 reviews

Charming 3-bedroom House In Annapolis Two Blocks From The Navy Stadium

apartment, Annapolis
This Annapolis vacation home in the Admiral Heights neighborhood is less than a mile from the Navy-Marine Corps Memorial Stadium and 1.5 miles from the U.S. Naval Academy, offering easy access to local attractions.
The three-bedroom, three-bathroom house sleeps eight guests and features a fully equipped kitchen, private patio, free Wi-Fi, laundry facilities, and parking.

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.

Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.8 11 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This Annapolis townhouse, centrally located near Navy Stadium and two miles from the United States Naval Academy, offers easy access to major attractions.
The 3,190-square-foot property boasts a spacious layout sleeping up to 10 guests, featuring a chef's kitchen with GE Café appliances, a finished basement, and proximity to Heineman Park, Harts Cove, and a community pool.
The Buccaneer - Annapolis, MD
No reviews

The Buccaneer

house, Annapolis
This family-friendly house is located 2.5 miles from Historic Downtown Annapolis and Eastport, 3 miles from the U.S. Naval Academy, and within walking distance to Capital SUP on Back Creek for paddle board and kayak rentals, the Annapolis Maritime Museum, and Bert Jabin Yacht Yard.
This property accommodates up to 9 guests with 3 bedrooms and 2 bathrooms, featuring a fully equipped entertainment room with foosball, arcade, and theater room, a four-season patio, and a custom built-in dining table for 6-8 guests.
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
This Annapolis vacation home is located in the Historic District, within walking distance of St. John's College, Chase Lloyd House, and Hammond-Harwood House. The U.S. Naval Academy and French Soldiers Monument are also a short walk away. The property has excellent user, location, and cleanliness ratings.
This 1950 square foot house has four bedrooms and can accommodate eight guests. It includes a fully equipped kitchen, a fireplace, a balcony, a garden, a spa, parking, and a gas grill.
Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 256 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, Annapolis
This waterfront cottage is located in West Annapolis, a short walk from the US Naval Academy's Gate 8 and a 1.5-mile walk to Annapolis City Dock, making it easy to explore the city's historic attractions and vibrant waterfront. This charming cottage enjoys excellent user, location and cleanliness ratings.
The 700 square foot cottage comfortably sleeps four guests and features a fully equipped kitchen, a screened-in porch, and a private dock with stunning views of Weems Creek. Guests can enjoy amenities like a fire pit, picnic area, paddle boards, kayaks, and a 17' Boston Whaler (for experienced boaters at an extra cost).

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.

Across From Stadium - Walk To Downtown Annapolis! - Annapolis, MD
9.7 199 reviews

Across From Stadium - Walk To Downtown Annapolis!

apartment, Annapolis
This Annapolis vacation rental is conveniently located just half a mile from Helen Avalynne Tawes Garden and a short drive from the U.S. Naval Academy. The property has received excellent ratings for location, cleanliness, and overall user experience. This 4-bedroom home can comfortably accommodate up to 10 guests. Enjoy the modern amenities, including a fully equipped kitchen, a fireplace, a balcony, and a garden with barbecue grills.

Best Annapolis, MD lodging with a balcony

Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & Parking

apartment, Annapolis
Two Historic Rowhomes In Downtown Annapolis - Annapolis, MD
10 1 review

Two Historic Rowhomes In Downtown Annapolis

apartment, Annapolis
Waterfront Suite With Views Of Annapolis From Prime Eastport Location - Annapolis, MD
9.8 6 reviews

Waterfront Suite With Views Of Annapolis From Prime Eastport Location

apartment, Annapolis
Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown - Annapolis, MD
10 26 reviews

Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown

apartment, Highland Beach

Best Annapolis, MD lodging with a kitchen

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian - Annapolis, MD
10 1 review

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian

apartment, Annapolis
Dog Friendly! Next To Navy Stadium And Dta Shuttle! - Annapolis, MD
10 12 reviews

Dog Friendly! Next To Navy Stadium And Dta Shuttle!

apartment, Annapolis
Historic Annapolis Charmer <1mile To Nmc Stadium - Annapolis, MD
9.8 7 reviews

Historic Annapolis Charmer <1mile To Nmc Stadium

apartment, Annapolis
Navy Weekend Haven, Family-friendly Luxury Home W Fenced-in Backyard & Parking - Annapolis, MD
10 15 reviews

Navy Weekend Haven, Family-friendly Luxury Home W Fenced-in Backyard & Parking

apartment, Annapolis

Best Annapolis, MD lodging with laundry available

Spacious 5 Br House - 5 Min Walk To N-mc Stadium! - Annapolis, MD
9.8 6 reviews

Spacious 5 Br House - 5 Min Walk To N-mc Stadium!

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

Downtown Annapolis King George 3rd Floor Hideaway

apartment, Annapolis
Historic Happy Home Steps From Main Street W Private Yard, Screened-in Porch & Parking - Annapolis, MD
10 36 reviews

Historic Happy Home Steps From Main Street W Private Yard, Screened-in Porch & Parking

apartment, Annapolis
Adorable Home Steps From Navy Stadium! - Annapolis, MD
No reviews

Adorable Home Steps From Navy Stadium!

apartment, Annapolis
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