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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.

Bayridge House By Quiet Waters, Thomas Point Parks - Annapolis, MD
9.5 16 reviews

Bayridge House By Quiet Waters, Thomas Point Parks

apartment, Annapolis
This brand-new Annapolis house, located near Eastport in a secluded wooded area, offers easy access to Quiet Waters Park, various restaurants (Grump's Café, Annapolis Smokehouse, Caliente Grill, Starbucks), West Marine, and a Giant grocery store, all within a short walk or drive.
The 2-bedroom, 1-bathroom rental sleeps 5 guests comfortably, featuring a fully equipped kitchen, washer/dryer, queen-sized beds, TVs in each room, a fold-out bed, ample off-street parking (3-4 vehicles), and a nautical-themed interior.

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.

Experience Historic Annapolis Stay In This Unique Dual-suite Home With On-site Parking - Annapolis, MD
10 1 review

Experience Historic Annapolis Stay In This Unique Dual-suite Home With On-site Parking

apartment, Annapolis
This Annapolis rental, located in the Historic District, is two blocks from Main Street and four blocks from the U.S. Naval Academy.
The two-unit apartment, accommodating up to 10 guests, features fully equipped kitchens, high-speed internet, in-unit laundry, keyless entry, and on-site parking for one car.

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.

Charming Annapolis Victorian - Annapolis, MD
10 137 reviews

Charming Annapolis Victorian

apartment, Annapolis
This three-story apartment is ideally located within walking distance from the US Naval Academy, the USNA Stadium and downtown Annapolis. It's the perfect place to stay for Commissioning Week, with a minimum of seven nights required. It has been rated excellent by users for its location, cleanliness, and amenities.
The apartment has six bedrooms and can accommodate up to 12 guests. It features a spacious and multi-level layout with a kitchen equipped with a fridge, freezer, microwave oven, and dishwasher. The apartment also includes a jacuzzi, a terrace or balcony, a garden, parking, and air conditioning. Pets are allowed, and the apartment is family-friendly with internet access.
Annapolis-4 Bed 3 Bath, 2 Blocks From Stadium. - Annapolis, MD
9.5 85 reviews

Annapolis-4 Bed 3 Bath, 2 Blocks From Stadium.

apartment, Annapolis
This newly renovated home is conveniently located in Annapolis, just a short walk from downtown and the Naval Academy Stadium, making it easy to explore the city's attractions. It has received excellent ratings for location, cleanliness, and overall user experience.
The house features four bedrooms and three bathrooms, comfortably accommodating up to ten guests. Guests can enjoy modern amenities like air conditioning, a fully equipped kitchen with a dishwasher, a garden, a fitness center, and even a jacuzzi for added relaxation.
Serene Sunsets At Historic Waterfront Home - Annapolis, MD
9.6 34 reviews

Serene Sunsets At Historic Waterfront Home

apartment, Mayo
This apartment is located in Hillsmere, a neighborhood in Annapolis, Maryland, just 4 miles from downtown Annapolis and the U.S. Naval Academy, offering a peaceful retreat with stunning views. It has received excellent user ratings and is perfect for a relaxing getaway.
This 5-bedroom, 2-bathroom rental comfortably sleeps 10 guests. Enjoy modern amenities, outdoor spaces with a patio, deck, BBQ grill, and pier, and kayaking on the tidal pond.
Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking,  Pets+kids - Annapolis, MD
10 54 reviews

Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking, Pets+kids

apartment, Annapolis
This three-bedroom Annapolis rental, located in Admiral Heights, is 1.6 miles from the U.S. Naval Academy and 0.5 miles from People's Brewer Hill Cemetery.
This smoke-free apartment features a private fenced yard, patio, barbecue grills, a fireplace, and accommodates up to six guests with amenities including a refrigerator, microwave, and Wi-Fi.

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.

Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 257 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).

Best Annapolis, MD lodging with a balcony

Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
No reviews

Chapel Gate 3br Steps To City Dock & Naval Academy

apartment, Annapolis
Historic Annapolis Home Walk To Downtown 3br - Annapolis, MD
No reviews

Historic Annapolis Home Walk To Downtown 3br

apartment, Annapolis
Bayridge House By Quiet Waters, Thomas Point Parks - Annapolis, MD
No reviews

Bayridge House By Quiet Waters, Thomas Point Parks

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

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis

Best Annapolis, MD lodging with a kitchen

Charming  Living Room In Beautiful Annapolis With Ac Discount Long Stay - Annapolis, MD
No reviews

Charming Living Room In Beautiful Annapolis With Ac Discount Long Stay

B&B, Annapolis
Hillsmere Hideaway - Annapolis, MD
9.9 98 reviews

Hillsmere Hideaway

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
Private Annapolis Inlaw Apartment - Annapolis, MD
9.8 369 reviews

Private Annapolis Inlaw Apartment

apartment, Annapolis

Best Annapolis, MD lodging with laundry available

Charming Barn In Annapolis For A Relaxing Getaway Not A Room Just A Mattress - Annapolis, MD
No reviews

Charming Barn In Annapolis For A Relaxing Getaway Not A Room Just A Mattress

apartment, Annapolis
Luxury Townhome Mins To Downtown Annapolis, W Multiple Ensuite Bedrooms & Parking - Annapolis, MD
10 1 review

Luxury Townhome Mins To Downtown Annapolis, W Multiple Ensuite Bedrooms & Parking

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
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