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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.

Cute Bungalow Blocks To Stadium - Annapolis, MD
9.9 81 reviews

Cute Bungalow Blocks To Stadium

apartment, Annapolis
This stylish two-bedroom house is located in Annapolis' Germantown neighborhood, just two blocks from Navy-Marine Corps Memorial Stadium and an 8-minute drive from the USNA and Downtown Annapolis. The home has received excellent ratings for location, cleanliness, and overall user experience.
The house is a two-floor home with a capacity of 6 guests. This Annapolis home offers amenities like a fully equipped kitchen, air conditioning, a fenced-in backyard, and a covered, screened-in eating area.

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.

Family/group Retreat Near Usna Stadium & Downtown Annapolis; Private Yard - Annapolis, MD
10 3 reviews

Family/group Retreat Near Usna Stadium & Downtown Annapolis; Private Yard

apartment, Annapolis
This Annapolis vacation rental, located in the Admiral Heights neighborhood, is approximately one mile from the US Naval Academy Stadium, 1.6 miles from Anne Arundel Medical Center, and two miles from downtown Annapolis.
This three-bedroom, two-bathroom home offers 1190 square feet of living space, including a private backyard with a fire pit, a fully equipped kitchen, and amenities like a 65" flat-screen TV; it comfortably sleeps seven guests.

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.

Quail House - 1926 Four Bedroom Home In Annapolis - Annapolis, MD
9.9 566 reviews

Quail House - 1926 Four Bedroom Home In Annapolis

apartment, Annapolis
This charming bed and breakfast is located in the Homewood neighborhood, just a short walk from Annapolis's historic district, shopping areas, and the Navy stadium. It offers a peaceful escape from the city's hustle and bustle, with a spacious yard and gardens, and has earned excellent ratings for location, cleanliness, and overall experience.
The home features a unique blend of original details and modern touches, with an open-air floor plan, exposed wall sheathing, and a spiral staircase leading to the loft. Guests can enjoy a cozy living room, dining room, and front porch, along with amenities like a kitchenette, cable TV, Wi-Fi, a fire pit, and access to books and magazines.
Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown - Annapolis, MD
10 1 review

Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown

apartment, Annapolis
This newly built vacation rental in Annapolis's Bestgate area is located 3 miles from the United States Naval Academy, 2 miles from Navy-Marine Corps Memorial Stadium, and 3 miles from the Annapolis Historic District, with Anne Arundel Medical Center 1 mile away.
This spacious 3000 square foot house offers 4 bedrooms, 4 bathrooms, and accommodates up to 9 guests, featuring a unique rooftop bedroom with a wet bar and patio, a full kitchen, air conditioning, terrace, parking with an EV charger, and is pet-friendly.
Charming Downtwn Home- Private Parking Patio&yard! - Annapolis, MD
10 156 reviews

Charming Downtwn Home- Private Parking Patio&yard!

apartment, Annapolis
This family-friendly vacation home is located in Annapolis's city center, a short walk from the U.S. Naval Academy and the Annapolis Civil Rights Plaque. The house has earned excellent ratings for location, cleanliness, and overall user experience.
This 1500-square-foot home comfortably accommodates up to 10 guests in its 3 bedrooms. Enjoy a fully equipped kitchen, a relaxing garden, a spa, and a terrace, all within a smoke-free environment.
Annapolis Charm Bright 3br In Downtown - Annapolis, MD
9.6 28 reviews

Annapolis Charm Bright 3br In Downtown

apartment, Annapolis
This Annapolis vacation home is centrally located, within a 10-minute walk of People's Cemetery, Maryland Hall for Creative Arts, and the Ballet Theater of Maryland, and 1.7 miles from the U.S. Naval Academy.
This three-bedroom, two-bathroom house sleeps eight guests and offers a fully equipped kitchen, free Wi-Fi, a private patio, and parking; nearby attractions include the U.S. Naval Academy and various cultural venues.

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.

Brand New. 1.5 Blocks To Westin.1st Floor Bed/bath - Annapolis, MD
10 131 reviews

Brand New. 1.5 Blocks To Westin.1st Floor Bed/bath

apartment, Annapolis
This four-bedroom, three-bathroom Annapolis home is located in the Homewood neighborhood, just a short walk from the Westin Hotel and half a mile from the stadium.
The 2,590-square-foot apartment comfortably sleeps 10 guests and features modern design, a gourmet kitchen with high-end appliances, a garden, a spa, and off-street parking.

Best Annapolis, MD lodging with a balcony

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

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
Historic Annapolis Hideaway Steps To Usna And Main St W Private Patio & Parking - Annapolis, MD
10 25 reviews

Historic Annapolis Hideaway Steps To Usna And Main St W Private Patio & Parking

apartment, Annapolis
Historic Row Home | Hot Tub - 1 Block From Gate 1! - Annapolis, MD
9.0 10 reviews

Historic Row Home | Hot Tub - 1 Block From Gate 1!

apartment, Annapolis
Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis - Annapolis, MD
10 4 reviews

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis

apartment, Annapolis

Best Annapolis, MD lodging with a kitchen

Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
9.5 15 reviews

Chapel Gate 3br Steps To City Dock & Naval Academy

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
Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 257 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, Annapolis
Upscale Condo In Annapolis W/private Parking - Annapolis, MD
10 4 reviews

Upscale Condo In Annapolis W/private Parking

apartment, Annapolis

Best Annapolis, MD lodging with laundry available

Walk To Main St & City Dock From Historic Downtown Dog-friendly Apartment - Annapolis, MD
10 2 reviews

Walk To Main St & City Dock From Historic Downtown Dog-friendly Apartment

apartment, Annapolis
Eastport Cottage Charm 4 Blocks To Downtown - Annapolis, MD
10 1 review

Eastport Cottage Charm 4 Blocks To Downtown

apartment, Annapolis
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
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
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