Compare temporary rentals in Annapolis, MD from 100+ providers!

728 available short term rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Annapolis, MD short term rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

Cozy 1st Floor King George One Bedroom Apartment Right Across From Usna - Annapolis, MD
9.8 36 reviews

Cozy 1st Floor King George One Bedroom Apartment Right Across From Usna

apartment, Annapolis
This apartment is located in Annapolis' Historic District, just a short walk from the U.S. Naval Academy and other historical landmarks like the John Smith House. It has received excellent user ratings.
This one-bedroom rental comfortably sleeps up to four guests and features a full kitchen, a terrace, a garden, and parking. You'll also have access to modern amenities like free Wi-Fi, a washer and dryer, and a sofa bed.

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.

Private Room In Arnold/annapolis - Annapolis, MD
9.9 27 reviews

Private Room In Arnold/annapolis

apartment, Arnold
This Arnold bed and breakfast offers a private first-floor retreat, a 10-minute drive from Sandy Point State Park, Annapolis Harbor, and downtown Annapolis.
The guesthouse features one bedroom, one bathroom, a family room, patio access, laundry facilities, and accommodates up to two guests, boasting amenities such as air conditioning, internet, a Jacuzzi, and fitness center access.

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.

Waterfront Retreat | Dock, Views, Near Annapolis - Annapolis, MD
10 6 reviews

Waterfront Retreat | Dock, Views, Near Annapolis

apartment, Mayo
This waterfront condo on Ramsay Lake, flowing into the South River, offers approximately 100 feet of private waterfront and is located 20 miles from downtown Annapolis.
This family-friendly condo sleeps 11 and features a private dock with direct lake and river access, a home gym, a dedicated kids' hangout area, and is within 1 mile of Mayo Beach Park and Beverly Triton Beach.
Restful And Charming Home In Eastport - Annapolis, MD
No reviews

Restful And Charming Home In Eastport

apartment, Annapolis
This apartment is located in Eastport, Annapolis, just a short drive from the historic downtown and the US Naval Academy, offering easy access to the city's attractions. The neighborhood is charming and quiet, making it a perfect escape from the hustle and bustle of the city.
This comfortable home features three bedrooms, accommodating up to six guests, and includes a fully equipped kitchen, washer and dryer, and a private outdoor area with a dining table and fire pit. Enjoy the convenience of a Jacuzzi, a spa, and a garden, along with the unique experience of backyard chickens.
Cozy Stay In Downtown Naptown - Annapolis, MD
9.9 33 reviews

Cozy Stay In Downtown Naptown

apartment, Annapolis
This Lafayette Avenue apartment offers a central Annapolis location, within walking distance of the U.S. Naval Academy, the downtown area, and the city's waterfront.
This three-bedroom, two-bathroom rental sleeps eight guests and features a fully equipped kitchen, fast Wi-Fi, and private outdoor space.
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.

Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.9 24 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This 2,400 sq ft, 1.5-story townhouse in Annapolis, located a short walk from the stadium, provides convenient access to events and a shared neighborhood dock for waterfront enjoyment.
This pet-friendly residence accommodates up to 10 guests with three bedrooms and three bathrooms, featuring a chef's kitchen with GE Café appliances, a finished basement, and keypad entry.

Best Annapolis, MD lodging with a balcony

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! - Annapolis, MD
9.6 104 reviews

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

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

Serene Sunsets At Historic Waterfront Home

apartment, Mayo
Downtown Annapolis Charming 2 Bdr Townhome - Annapolis, MD
No reviews

Downtown Annapolis Charming 2 Bdr Townhome

apartment, Annapolis
Charming Charles -Walkable Downtown Annapolis Home - Annapolis, MD
10 10 reviews

Charming Charles -Walkable Downtown Annapolis Home

apartment, Annapolis

Best Annapolis, MD lodging with a kitchen

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian - Annapolis, MD
9.9 14 reviews

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian

apartment, Annapolis
Travel Respite For The Ladies. Safe Secure Lodging - Annapolis, MD
No reviews

Travel Respite For The Ladies. Safe Secure Lodging

apartment, Annapolis
Nautical Cottage In Annapolis - Annapolis, MD
9.7 21 reviews

Nautical Cottage In Annapolis

apartment, Annapolis
Uptown Condo W 2 Parking Spots - Annapolis, MD
10 17 reviews

Uptown Condo W 2 Parking Spots

apartment, Annapolis

Best Annapolis, MD lodging with laundry available

Captains Quarters | Waterfront & Pool - Annapolis, MD
10 117 reviews

Captains Quarters | Waterfront & Pool

apartment, Annapolis
Family Home On Mayo Peninsula | Deck | Sleeps 10 - Annapolis, MD
9.9 15 reviews

Family Home On Mayo Peninsula | Deck | Sleeps 10

apartment, Mayo
Newly Renovated 1-bedroom On Spa Creek - Annapolis, MD
9.9 27 reviews

Newly Renovated 1-bedroom On Spa Creek

apartment, Annapolis
Eastport 3 Bedroom Cottage: Walk To Downtown - Annapolis, MD
10 1 review

Eastport 3 Bedroom Cottage: Walk To Downtown

apartment, Annapolis
©2026 cozycozy.com