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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.

The Midship Quarters - Annapolis, MD
10 48 reviews

The Midship Quarters

apartment, Annapolis
This newly renovated three-bedroom house on Prince George Street in Annapolis' downtown offers prime access to shops, restaurants, and is within walking distance of St. John's College and the U.S. Naval Academy.
Sleeping up to nine guests, this Annapolis rental boasts a fully equipped kitchen with dishwasher, in-house fitness center, private garden, free on-site parking for 2-3 vehicles, and a nautically 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.

Just A Half-mile From Chesapeake Bay & Beaches - Annapolis, MD
No reviews

Just A Half-mile From Chesapeake Bay & Beaches

B&B, Annapolis
This historic inn in Annapolis offers a unique lodging experience within a renowned historic district, providing convenient access to significant American history landmarks.
This bed and breakfast features one bedroom and one bathroom, accommodating up to two guests with amenities including air conditioning and WiFi, with valet parking available for an additional fee.

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.

4 Bedrooms, 7 Beds, 3 Bath Completely Updated - Annapolis, MD
9.9 137 reviews

4 Bedrooms, 7 Beds, 3 Bath Completely Updated

apartment, Annapolis
This Annapolis vacation home is located near the headwaters of Weems Creek, offering a peaceful setting close to Annapolis's attractions.
This spacious, single-family home features four bedrooms, three bathrooms, and sleeps eight, boasting a fully equipped kitchen, a private backyard with a deck and grill overlooking Weems Creek, a PS5, and a basement family room with a pull-out bed.
Spacious Historic Home With Private Parking In The Heart Of Downtown Annapolis - Annapolis, MD
10 6 reviews

Spacious Historic Home With Private Parking In The Heart Of Downtown Annapolis

apartment, Annapolis
This pet-friendly Annapolis vacation rental is located in the Historic District, within walking distance of the Maryland State House and close to Jonas Green and Sandy Point State Parks.
The three-bedroom, three-bathroom apartment sleeps eight, offering amenities such as a fully equipped kitchen, Wi-Fi, a private terrace, on-site parking, and a jetted tub.
Historic + Modern Home | Just Steps To Waterfront - Annapolis, MD
10 49 reviews

Historic + Modern Home | Just Steps To Waterfront

apartment, Annapolis
This Fleet Street townhouse is located in downtown Annapolis, a short walk from City Dock, Main Street, and the U.S. Naval Academy.
This renovated two-bedroom, one-bathroom rental sleeps seven guests and features a fully equipped kitchen with stainless steel appliances, in-unit laundry, and family-friendly amenities like a pack-and-play and high chair available upon request.
Annapolis By St John College Cat Food $50 - Annapolis, MD
No reviews

Annapolis By St John College Cat Food $50

B&B, Annapolis
This upscale bed and breakfast in Annapolis offers a prime location, placing you within easy walking distance of the historic waterfront district, the Maryland State House, and the United States Naval Academy.
This accommodation provides one bedroom with a guest capacity of two, featuring internet access and a kitchen, serving as a comfortable base for exploring Annapolis's restaurants and boutiques.

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.

Seabrook Downtown 3br Garage  Walk To Waterfront - Annapolis, MD
8.8 12 reviews

Seabrook Downtown 3br Garage Walk To Waterfront

apartment, Annapolis
This newly renovated 3-bedroom, 2-bathroom apartment is located in a quiet downtown Annapolis residential neighborhood, a 10-minute walk to Main Street and a 16-minute walk to City Dock and the Naval Academy.
This home accommodates up to 6 guests and features a fully stocked kitchen with a fridge, freezer, microwave, and dishwasher, plus central air conditioning and fast Wi-Fi.

Best Annapolis, MD lodging with a balcony

Inn On Main Annapolis - Annapolis, MD
8.2 272 reviews

Inn On Main Annapolis

B&B, Annapolis
Serene Sunsets At Historic Waterfront Home - Annapolis, MD
9.6 34 reviews

Serene Sunsets At Historic Waterfront Home

apartment, Mayo
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
Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 252 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, Annapolis

Best Annapolis, MD lodging with a kitchen

The Red Door Cottage - Pet-friendly! - Annapolis, MD
10 36 reviews

The Red Door Cottage - Pet-friendly!

apartment, Annapolis
3br/2ba Annapolis Cottage - Annapolis, MD
10 222 reviews

3br/2ba Annapolis Cottage

apartment, Annapolis
Beautiful Private Room And Bath - Edge Of Eastport - Annapolis, MD
9.9 103 reviews

Beautiful Private Room And Bath - Edge Of Eastport

apartment, Annapolis
Carriage House With Character! - Annapolis, MD
10 11 reviews

Carriage House With Character!

apartment, Riva

Best Annapolis, MD lodging with laundry available

6br Dog Friendly | Fireplace | Chef's Kitchen - Annapolis, MD
10 3 reviews

6br Dog Friendly | Fireplace | Chef's Kitchen

apartment, Highland Beach
Annapolis, Maryland:  Charming Cottage 1 Block Fro - Annapolis, MD
9.5 66 reviews

Annapolis, Maryland: Charming Cottage 1 Block Fro

apartment, Highland Beach
Waterfront Retreat | Dock, Views, Near Annapolis - Annapolis, MD
10 5 reviews

Waterfront Retreat | Dock, Views, Near Annapolis

apartment, Mayo
Bay View Retreat | 5br / 5.5 Bath | Balconies - Annapolis, MD
No reviews

Bay View Retreat | 5br / 5.5 Bath | Balconies

apartment, Annapolis
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