Vacation rentals in Annapolis

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Dog friendly vacation rentals in Annapolis

Superhost
Home in Edgewater
4.91 out of 5 average rating, 145 reviews

House in Edgewater Maryland

TimothyRating, 5 stars2 weeks ago
The house was beautiful and clean. The lication was great! Too bad it rain during out stay so we couldn’t enjoy the pool and the backyard. Thank you!
Guest favorite
Condo in Annapolis
4.94 out of 5 average rating, 395 reviews

Brand New Reno in Historic Dist w 2 Parking spots

MichelleRating, 5 stars2 weeks ago
Great stay in Annapolis. The property is located at the end of a quiet, dead end tree-lined street. A short and pleasant walk to the heart of Annapolis with dining and shopping options along the way. The property was clean and appeared exactly as the shown in the photos.
Guest favorite
Cottage in Deale
4.82 out of 5 average rating, 181 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

BobRating, 5 stars3 weeks ago
Shawn's place is great! It is well-cared for and has everything you need to enjoy the indoors and the outdoors. The views of the water are beautiful and you can spend a lot of time watching the different birds. Getting there is easy and not far from restaurants and grocery stores. Shawn makes you feel special and wants to ensure you have a wonderful stay. Hope to go back soon.
Guest favorite
Cottage in Annapolis
4.93 out of 5 average rating, 202 reviews

Secluded Cottage_ A+ Amenities in Historic Dwntwn

RogerRating, 5 stars4 weeks ago
Perfectly located, walked everywhere. Clean and comfortable.
Top guest favorite
Home in Annapolis
4.99 out of 5 average rating, 149 reviews

Crab Cakes and Football Historic District

KimRating, 5 stars2 weeks ago
Everything was great! Would stay again.
Superhost
Home in Annapolis
4.87 out of 5 average rating, 179 reviews

Charming Annapolis Water View Home

ManningRating, 5 stars4 weeks ago
This house is uncommonly beautiful. There is something in every space worthy of contemplation whether it is coffee table in the living room that has a turn of the century industrial feel to the lacquered kitchen countertop that has sealed in the natural beauty. I spent the weekend in awe of its intricacies. I was in town for a wedding with my family, but noted how the whole house including the outdoor space included everything a beachfront house would have to enjoy an extended summer vacation for the whole family. Outdoor space was well equipped for outdoor activities and entertainment with fire pits, grills, hot tub, a plugin cooler for outdoor use. I only wish we’d been better suited to enjoy every aspect of the amenities provided. My favorite thing about this place was the view of the Chesapeake in all of her glory on full display from the living room window. Delightful.
Guest favorite
Cottage in Glen Burnie
4.92 out of 5 average rating, 190 reviews

Home away from home

WalterRating, 5 stars3 weeks ago
a great little hideaway for your trip to the Baltimore and Anapolis area. a great host and comfortable place to stay!
Top guest favorite
Guesthouse in Annapolis
4.99 out of 5 average rating, 136 reviews

Garden View, a spacious 1 bedroom with loft.

MarieRating, 5 stars1 week ago
Sally’s place was a perfect ‘getaway’ to get some work and dissertation writing in. She was super nice to bring me an office chair, and her husband provided freshly baked cookies! My dog, Bagel, loved watching the wildlife out the window. The neighborhood is cute and peaceful but also close to anything you want to do or eat. The thoughtful touches and top-notch stock of kitchen items made my stay so enjoyable. I didn’t get to enjoy the backyard amenities but will be back for that and to explore more. Wonderful place and hosts, plus an adorable furry host!

Other great vacation rentals in Annapolis

Top guest favorite
Home in Annapolis
4.99 out of 5 average rating, 86 reviews

Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths

ChadRating, 5 stars1 week ago
The house is easy to find and has a great outdoor seating area. The house and linens were very clean and Sekai even provided fresh fruit upon arrival! The stocked Kurig pods were very handy and appreciated in the morning as well. From this location you have easy access to downtown Annapolis and all of its history. If you go the other way out of the neighborhood, you can browse the mall and TownCentre for all your other shopping needs. This is a pet friendly house that you would not know there had ever been a dog in there. Fortunately, ours was well behaved so you still won't know a pet was ever there! He enjoyed walking the large private yard.
Top guest favorite
Guesthouse in Annapolis
5 out of 5 average rating, 25 reviews

Eastport Gem ~ Walk to Downtown Annapolis

AaronRating, 5 stars1 week ago
The home was spotless, comfortable, and perfectly located—just a short walk to the historic downtown, waterfront, and great restaurants. The host was friendly and responsive, offering helpful local tips and making check-in a breeze. The space was cozy and well-stocked with everything we needed for a relaxing getaway.
Guest favorite
Loft in Riva
4.95 out of 5 average rating, 120 reviews

New Loft w/South River view from treehouse deck!

TristanRating, 5 stars3 weeks ago
It was a pleasure staying in this loft! Joe made the instructions very clear. It was everything that the description stated! Only a short uber ride to downtown Annapolis which made it even better.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 12 reviews

Historic Downtown Annapolis Gem

BethanyRating, 5 stars2 weeks ago
This home is right in downtown Annapolis. You can walk to many historic sites, restaurants, and bars. There is no parking, so you must park in one of the garages and walk to the house - but it isn't far. Street parking is limited to 2 hours for non-permit holders. This was one of my favorite airbnbs in Annapolis (and I've stayed in many). It was exactly as pictured/described. It was bigger than expected with lots of space for a larger group. The living room was nice with lots of seating and a large tv. We used the pullout sofa in the second living area and it was super comfortable. The bedrooms and bathrooms were very nice - great showers and deep soaker tub in the en suite. I slept in the king bed in the back bedroom and it was wonderful. The kitchen and dining area were very nice and we gathered there much of the time. We enjoyed the front porch for morning coffee and evening drinks. The back patio was also another nice space to sit and relax.
Top guest favorite
Guest suite in Annapolis
5 out of 5 average rating, 27 reviews

Pristine, Private 1 Bed/1 Bath Guest Apartment

MieRating, 5 stars3 weeks ago
When you book Fox Haven, you not only get a tranquil sanctuary, but the most gracious and communicative host who anticipates your every possible need. The space is thoughtfully designed and equipped for convenience and is located at the end of dead end street in a quiet residential area in the middle of all the action. A friend who came to visit me was so impressed that she was voluntarily raving about the place to others. I look forward to returning time and again.
Top guest favorite
Guesthouse in Annapolis
5 out of 5 average rating, 7 reviews

Eastport Coastal Cottage - Patio - Walk Downtown!

MeganRating, 5 stars1 month ago
This was the cutest guest house! Stayed here for a bachelorette weekend for one of my friends and it was perfect. We were able to walk everywhere we needed to and was the perfect size for the five of us. Conor gave me some recommendations of places to eat/things to do and they were all wonderful. I would definitely recommend this place for your next visit to Annapolis!
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 40 reviews

Bay Home in Annapolis with Private Dock

DavidRating, 5 stars1 month ago
The description of Joel's Annapolis home is an accurate description of his wonderful home. The most outstanding features of this property are: the waterfront location --> unobstructed panoramic views; serene setting on a quiet street and there are lots of other pluses. The house was super comfortable. Everything was in working order. I appreciated the workout equipment --> not lots of stuff but enough to get some indoor exercise that I like to do each day. Walking up and down the street --> neighbors were all very friendly. The kitchen is fabulous. It only took about 15 to 20 minutes to get to the center of things to do and see in Annapolis. While we did not use much of the outside furniture, the outside furniture is plentiful and looks comfortable. A big thing for us is cleanliness --> the house is immaculate. We will probably make a return trip in the future and would appreciate the opportunity to stay here again.
Superhost
Townhouse in Annapolis
4.91 out of 5 average rating, 142 reviews

Beautiful Townhome Downtown Annapolis

StephenRating, 5 stars2 weeks ago
The house was absolutely spotless! I mean.. SPOTLESS!!! It had everything needed for a comfortable stay, with high-quality furnishings in both the rooms and kitchen. We self-catered several meals and found the kitchen fully equipped with everything we required. Sharon was wonderful, very responsive and incredibly helpful!

Quick stats about vacation rentals in Annapolis

  • Total rentals

    650 properties

  • Total number of reviews

    32K reviews

  • Family-friendly rentals

    460 properties are a good fit for families

  • Pet-friendly rentals

    200 properties allow pets

  • Rentals with a pool

    40 properties have a pool

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

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 hiking trails in Annapolis?

    Annapolis has several scenic trails such as the 3.3-mile (5.3 km) Baltimore and Annapolis Trail and the shorter but equally beautiful 1.7-mile (2.7 km) Quiet Waters Park Trail. Both are suitable for varying skill levels.

  • 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.

  • What types of vacation rentals are available in Annapolis?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Annapolis. From over 390 house rentals to over 90 apartment rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

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

    Yes! Work meets play with ease at over 350 vacation rentals in Annapolis featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore