Annapolis vacation rentals

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Top-rated vacation rentals in Annapolis

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!
Jul 31 – Aug 7
$158 per night
4.94 out of 5 average rating, 305 reviews
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.
Nov 10 – 17
$85 per night
4.9 out of 5 average rating, 202 reviews
Guest favorite
Guesthouse in Annapolis
Chesapeake Birdhouse Studio
Private, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.
Aug 6 – 13
$105 per night
4.87 out of 5 average rating, 310 reviews

Popular amenities for Annapolis vacation rentals

Stay near Annapolis's top sights

Annapolis City Dock34 locals recommend
Navy-Marine Corps Memorial Stadium34 locals recommend
Graduate Annapolis11 locals recommend
Historic Inns of Annapolis8 locals recommend
Rams Head On Stage22 locals recommend
Boatyard Bar & Grill127 locals recommend

Annapolis home rentals

Guest favorite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
Apr 8 – 15
$900 per night
5.0 out of 5 average rating, 103 reviews
Guest favorite
Home in Annapolis
Sophisticated & Spacious Historic Home w/ Parking!
Feb 14 – 21
$492 per night
4.95 out of 5 average rating, 145 reviews
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
Feb 26 – Mar 5
$277 per night
4.94 out of 5 average rating, 283 reviews
Guest favorite
Home in Annapolis
Crab Cakes and Football Historic District
Jun 16 – 23
$399 per night
4.98 out of 5 average rating, 127 reviews
Guest favorite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
Oct 8 – 15
$395 per night
5.0 out of 5 average rating, 111 reviews
Guest favorite
Home in Annapolis
Charming house; walk to everywhere in Annapolis
Jun 18 – 25
$261 per night
4.99 out of 5 average rating, 145 reviews
Guest favorite
Home in Annapolis
Quiet Waterfront
Aug 28 – Sep 4
$332 per night
4.98 out of 5 average rating, 154 reviews
Guest favorite
Home in Annapolis
Charming Renovated Historic Home Downtown wparking
Jan 9 – 16
$298 per night
4.92 out of 5 average rating, 182 reviews
Guest favorite
Home in Cambridge
"Happy Campers" Waterfront Apartment!
Nov 26 – Dec 3
$135 per night
5.0 out of 5 average rating, 262 reviews
Guest favorite
Home in Annapolis
Chesapeake Comfort, Annapolis.
Aug 19 – 26
$320 per night
4.97 out of 5 average rating, 129 reviews
Guest favorite
Home in Edgewater
Spacious 3 Bedrooms House+Patio
May 2 – 9
$129 per night
4.96 out of 5 average rating, 51 reviews
Guest favorite
Home in Arnold
Private Arnold basement apt- Close to The Point!
Jul 24 – 31
$72 per night
4.93 out of 5 average rating, 15 reviews

Other great vacation rentals in Annapolis

Guest favorite
Guest suite in Annapolis
Private 2B Apt--less than 1 mi to Downtown
Nov 12 – 19
$133 per night
4.97 out of 5 average rating, 159 reviews
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Aug 29 – Sep 5
$173 per night
4.94 out of 5 average rating, 349 reviews
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Dec 14 – 21
$168 per night
4.96 out of 5 average rating, 326 reviews
Guest favorite
Apartment in Annapolis
Charming lower-level apartment in Annapolis
Jun 14 – 21
$111 per night
4.96 out of 5 average rating, 122 reviews
Guest favorite
Guest suite in Annapolis
Cozy Naptown Perch
May 5 – 12
$154 per night
4.96 out of 5 average rating, 162 reviews
Guest favorite
Guesthouse in Annapolis
Garden View, a spacious 1 bedroom with loft.
Sep 8 – 15
$167 per night
5.0 out of 5 average rating, 106 reviews
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
May 22 – 29
$162 per night
4.96 out of 5 average rating, 558 reviews
Guest favorite
Condo in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
Feb 10 – 17
$160 per night
4.95 out of 5 average rating, 340 reviews
Guest favorite
Guest suite in Edgewater
South River Park Apartment
May 23 – 30
$95 per night
4.89 out of 5 average rating, 434 reviews
Guest favorite
Apartment in Annapolis
Walk to Water, State House, USNA
Jan 4 – 11
$163 per night
4.92 out of 5 average rating, 106 reviews
Guest favorite
Cottage in Glen Burnie
Home away from home
Nov 2 – 9
$69 per night
4.92 out of 5 average rating, 136 reviews
Guest favorite
Condo in Annapolis
Funky Uptown Apt meets Downtown - Hist District
Mar 23 – 30
$106 per night
4.96 out of 5 average rating, 50 reviews

Quick stats about vacation rentals in Annapolis

Total rentals

650 properties

Rentals with dedicated workspaces

340 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

180 properties allow pets

Family-friendly rentals

450 properties are a good fit for families

Total number of reviews

28K reviews

Your guide to Annapolis

All About Annapolis

The capital of Maryland, Annapolis sits on the banks of Chesapeake Bay and is known for its historic neighborhoods and 18th-century Colonial, Georgian, and Victorian homes. With its reputation as the sailing capital of the United States, and home to the U.S. Naval Academy, Annapolis holds several significant historical credentials, including a founding that dates back to 1649. St. John's College, one of the oldest universities in the country, still stands proud on Annapolis soil.

Today, this prosperous East Coast city is known more for its thriving downtown Historic District with boutique shops, galleries, and architectural sites that provide a day of exploration before heading to the Eastport District, where the Annapolis culinary scene emphasizes locally sourced oysters, crabs, and scallops. For nightlife, West Street is where you will find several bars, clubs, and restaurants, many of which regularly host live music on the weekends.


The best time to stay in a vacation rental in Annapolis

Annapolis experiences drastic weather changes from season to season. The summer months tend to be hot and humid, with moderate precipitation and long pleasant nights. Several festivals occur during the summer days, like a Renaissance fair in a fictional 16th-century village with costumed events, vendors, and medieval-era arts and crafts. Or the weekly Wednesday Night Sailboat Races that take place from May through September.

The winter sees temperatures drop to below freezing with an occasional dusting of snow. However, Annapolis’ warm cafes and cozy street-side restaurants can make brisk days feel quite pleasant. The shoulder seasons are an excellent time to look for vacation rentals in Annapolis, as the spring weather conditions that are temperate also mark the beginning of the sailing season. The fall hosts a brilliant display of autumn hues in the treetops throughout the city with similar weather patterns to that of spring.


Top things to do in Annapolis

Annapolis Maritime Museum

This waterfront museum houses several exhibitions and displays that detail the area's maritime history and the ocean's significance in its economic, social, and cultural developments. Exhibits explain Chesapeake Bay’s unique ecological makeup and how it has impacted the fishing industry over the years. In addition, several art and photography displays highlight the region's social makeup through contributions by local and internationally renowned artists.

Historic London Town

Located just outside of Annapolis in the town of Edgewater, this 23-acre park is a recreation of a lost 18th-century colonial village that would have been common in the area at the time. A carpenter's shop, mayor's tenement, picnic areas, and ten acres of woodland and ornamental gardens are all waiting to be explored in the area. Recreated through a series of archeological discoveries, most of the buildings are full of everyday objects that would have been found and used at the time.

Lake Waterford Park

This 108-acre park is where the locals come to stretch out when the weather is nice. It includes a full lineup of recreational activities, from tennis courts to football fields. Walking trails and hiking paths meander through much of the wooded park, and there’s a 12-acre lake for spotting waterfowl and fishing from the shores.

Frequently Asked Questions

  • How is the weather in Annapolis?

    Annapolis has a temperate climate. Summers are hot and humid with temperatures around 85°F (29°C), while winters are chilly, around 40°F (4°C). Spring and autumn are mild, making these seasons popular for visiting.

  • What are some of the best things to do in Annapolis?

    Visitors to Annapolis can tour the United States Naval Academy, sail on the Chesapeake Bay, or explore the historic district. The Arts District is also popular for its galleries and studios.

  • What is the best time of year to visit Annapolis?

    Spring and fall are often suggested for a visit to Annapolis due to the mild and enjoyable weather. Spring brings the annual Annapolis Film Festival, and the U.S. Sailboat Show takes place in October, attracting a large number of visitors.

  • What are the best places to stay in Annapolis?

    Downtown Annapolis is frequently suggested as it's close to historic sites, restaurants, and shopping. Eastport, with its maritime charm, and West Annapolis, known for its quaint, village-like atmosphere, are also popular options.

  • What are the best places to visit in Annapolis?

    The Maryland State House, St. Anne's Episcopal Church, and the William Paca House are popular places to visit. The Annapolis Historic District and the Annapolis Maritime Museum are also frequently suggested.

  • What are some family activities to do in Annapolis?

    Families can explore the Maryland State House, navigate the stars at the Maryland Planetarium, or enjoy a day of fun at the Annapolis Maritime Museum. Children will also enjoy the interactive exhibits at the Chesapeake Children's Museum.

  • What are some of the best day trip ideas in Annapolis?

    A day trip by boat to St. Michael's, a charming historic town, is a great idea. You can also visit Sandy Point State Park for a beach day or journey to Baltimore, which is just 32 miles (51.5 km) away, for more city experiences.

  • Are there vacation rentals with a dedicated workspace in Annapolis?

    Yes! Work meets play with ease at over 340 vacation rentals in Annapolis featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Annapolis?

    Four-legged friends are welcome in Annapolis. Choose from more than 180 vacation rentals for guests traveling with pets.

  • Are there Annapolis vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Annapolis, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore