Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

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Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 562 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

6–13 Jul

₹9,351 per night

Guest favourite

Cottage in Annapolis

4.94 out of 5 average rating, 312 reviews

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!

3–10 Aug

₹14,870 per night

Guest favourite

Guest house in Annapolis

4.9 out of 5 average rating, 205 reviews

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.

28 Oct – 4 Nov

₹8,174 per night

Guest favourite

Guest house in Annapolis

4.87 out of 5 average rating, 312 reviews

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.

9–16 Sep

₹10,119 per night

Guest favourite

Guest house in Annapolis

4.97 out of 5 average rating, 155 reviews

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.

12–19 Jul

₹11,705 per night

Guest favourite

Flat in Crownsville

4.98 out of 5 average rating, 163 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

16–23 Aug

₹10,550 per night

Guest favourite

Guest house in Annapolis

4.99 out of 5 average rating, 104 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

23–30 Oct

₹32,358 per night

Guest favourite

Guest house in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

25 Oct – 1 Nov

₹9,954 per night

Guest favourite

Home in Annapolis

4.96 out of 5 average rating, 106 reviews

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit.

4–11 Feb

₹10,142 per night

Guest favourite

Loft in Annapolis

4.91 out of 5 average rating, 915 reviews

Step Out to Main Street From a Chic Loft

This loft apartment features an exquisite industrial-chic aesthetic where exposed brick walls and hardwood floors are accentuated by metallic textures and rustic items. Curl up with a book from the bookshelf or sink into the sofa to watch TV.

2–9 Jan

₹12,283 per night

Guest favourite

Guest suite in Annapolis

4.96 out of 5 average rating, 367 reviews

Our Annapolis Penthouse

This rental is private studio above our home in the Murray Hill neighborhood of Annapolis. Walk to town, upper West St. restaurants, Academy Stadium. It has a private entrance and it's own heat /AC control. Pool privileges may be offered.

8–15 Dec

₹9,602 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Annapolis holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Annapolis's top sights

Annapolis City Dock34 locals recommend

Navy-Marine Corps Memorial Stadium34 locals recommend

Graduate Annapolis11 locals recommend

Maryland State House81 locals recommend

Historic Inns of Annapolis8 locals recommend

Rams Head On Stage22 locals recommend

Other great holiday rentals in Annapolis

Guest favourite

Guest suite in Edgewater

4.89 out of 5 average rating, 436 reviews

South River Park Apartment

23–30 Dec

₹8,332 per night

Guest favourite

Home in Annapolis

4.99 out of 5 average rating, 197 reviews

Cape St Claire waterfront getaway

13–20 Nov

₹12,007 per night

Guest favourite

Guest suite in Arnold

4.84 out of 5 average rating, 496 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

19–26 Aug

₹9,802 per night

Guest favourite

Flat in Edgewater

4.92 out of 5 average rating, 398 reviews

Pet Friendly Garden Apartment Near Annapolis

1–8 Aug

₹10,278 per night

Guest favourite

Boat in Annapolis

4.94 out of 5 average rating, 351 reviews

Stay aboard the S/V MY STUDIO on Annapolis Harbor

1–8 Dec

₹16,552 per night

Guest favourite

Guest house in Annapolis

5.0 out of 5 average rating, 105 reviews

Garden View, a spacious 1 bedroom with loft.

28 Dec – 4 Jan

₹14,802 per night

Guest favourite

Guest suite in Annapolis

4.97 out of 5 average rating, 161 reviews

Private 2B Apt--less than 1 mi to Downtown

30 Oct – 6 Nov

₹12,740 per night

Guest favourite

Flat in Annapolis

4.94 out of 5 average rating, 31 reviews

Hillsmere Hideaway

8–15 Nov

₹11,086 per night

Show all

Quick stats about holiday rentals in Annapolis

Total rentals	640 properties
Rentals with dedicated workspaces	350 properties have a dedicated workspace
Rentals with a pool	40 properties have a pool
Pet-friendly rentals	180 properties allow pets
Family-friendly rentals	440 properties are a good fit for families
Total number of reviews	28T reviews

Holiday rentals in Annapolis

Top-rated holiday rentals in Annapolis

Guest suite in Arnold

Cottage in Annapolis

Guest house in Annapolis

Guest house in Annapolis

Guest house in Annapolis

Flat in Crownsville

Guest house in Annapolis

Guest house in Annapolis

Home in Annapolis

Loft in Annapolis

Guest suite in Annapolis

Home in Annapolis

Holiday rentals for every style

Flats

Houses

Hotels

Popular amenities for Annapolis holiday rentals

Stay near Annapolis's top sights

Other great holiday rentals in Annapolis

Guest suite in Edgewater

Home in Annapolis

Guest suite in Arnold

Flat in Edgewater

Boat in Annapolis

Guest house in Annapolis

Guest suite in Annapolis

Flat in Annapolis

Quick stats about holiday rentals in Annapolis

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore