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
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 2 – 9
$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.
Jul 11 – 18
$105 per night
4.87 out of 5 average rating, 307 reviews
Guest favorite
Guesthouse in Annapolis
Lil’ House - A Serene Tiny Home Experience
Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.
Sep 27 – Oct 4
$127 per night
4.97 out of 5 average rating, 150 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
Historic Inns of Annapolis8 locals recommend
Rams Head On Stage22 locals recommend
Boatyard Bar & Grill127 locals recommend
Graduate Annapolis11 locals recommend

Annapolis home rentals

Guest favorite
Home in Annapolis
New Hotel Chic
Nov 21 – 28
$170 per night
4.95 out of 5 average rating, 335 reviews
Guest favorite
Home in Annapolis
Cape St Claire waterfront getaway
Sep 4 – 11
$126 per night
4.99 out of 5 average rating, 195 reviews
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
Feb 7 – 14
$277 per night
4.94 out of 5 average rating, 278 reviews
Guest favorite
Home in Annapolis
Charming Renovated Historic Home Downtown wparking
Nov 14 – 21
$298 per night
4.92 out of 5 average rating, 181 reviews
Guest favorite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
Jan 5 – 12
$814 per night
4.97 out of 5 average rating, 112 reviews
Guest favorite
Home in Annapolis
Sophisticated & Spacious Historic Home w/ Parking!
Dec 4 – 11
$484 per night
4.95 out of 5 average rating, 145 reviews
Guest favorite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
Jun 20 – 27
$577 per night
5.0 out of 5 average rating, 107 reviews
Guest favorite
Home in Annapolis
Quiet Waterfront
Mar 13 – 20
$332 per night
4.98 out of 5 average rating, 154 reviews
Guest favorite
Home in Annapolis
Crab Cakes and Football Historic District
Apr 20 – 27
$399 per night
4.98 out of 5 average rating, 127 reviews
Guest favorite
Home in Crownsville
Severn River Waterfront Home
Dec 10 – 17
$339 per night
4.94 out of 5 average rating, 148 reviews
Guest favorite
Home in Annapolis
Charming Annapolis Escape - 3BR/2BA House
Sep 7 – 14
$393 per night
4.94 out of 5 average rating, 101 reviews
Superhost
Home in Annapolis
Spacious 3BR 2Bath Minutes from Downtown Annapolis
Jul 23 – 30
$219 per night
4.78 out of 5 average rating, 100 reviews

Other great vacation rentals in Annapolis

Guest favorite
Apartment in Edgewater
Pet Friendly Garden Apartment Near Annapolis
Aug 5 – 12
$98 per night
4.92 out of 5 average rating, 394 reviews
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Apr 19 – 26
$203 per night
4.96 out of 5 average rating, 322 reviews
Guest favorite
Guest suite in Annapolis
Our Annapolis Penthouse
Feb 15 – 22
$101 per night
4.96 out of 5 average rating, 363 reviews
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
May 20 – 27
$190 per night
4.94 out of 5 average rating, 304 reviews
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Aug 26 – Sep 2
$173 per night
4.94 out of 5 average rating, 349 reviews
Guest favorite
Guesthouse in Annapolis
Garden View, a spacious 1 bedroom with loft.
Nov 22 – 29
$160 per night
5.0 out of 5 average rating, 102 reviews
Guest favorite
Condo in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
Oct 26 – Nov 2
$160 per night
4.95 out of 5 average rating, 339 reviews
Guest favorite
Guest suite in Arnold
Coastal Comfort Suite Near Annapolis, Hottub, EV
Jun 25 – Jul 2
$134 per night
4.93 out of 5 average rating, 107 reviews
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
Nov 10 – 17
$204 per night
4.94 out of 5 average rating, 255 reviews
Guest favorite
Apartment in Annapolis
Charming lower-level apartment in Annapolis
Aug 17 – 24
$108 per night
4.96 out of 5 average rating, 122 reviews
Guest favorite
Loft in Annapolis
Soak up the Soothing Vibe at a Grayscale Annapolis Loft
May 27 – Jun 1
$183 per night
4.99 out of 5 average rating, 157 reviews
Guest favorite
Condo in Annapolis
Funky Uptown Apt meets Downtown - Hist District
Mar 29 – Apr 5
$112 per night
4.96 out of 5 average rating, 48 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.

  • How much does it cost to stay in apartment rentals in Annapolis?

    Experience the best of Annapolis with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore