Holiday houses in Annapolis
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Annapolis
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Annapolis holiday rentals
Other great holiday rentals in Annapolis
Guest favourite
Apartment in Edgewater
4.92 out of 5 average rating, 398 reviewsPet Friendly Garden Apartment Near Annapolis
7–14 Sep
$221 NZD per night
Guest favourite
Guesthouse in Annapolis
4.99 out of 5 average rating, 104 reviewsCoastal Waterfront 1 Bedroom Cottage
6–13 Nov
$709 NZD per night
Guest favourite
Guest suite in Edgewater
4.89 out of 5 average rating, 436 reviewsSouth River Park Apartment
6–13 Dec
$189 NZD per night
Guest favourite
Guest suite in Arnold
4.85 out of 5 average rating, 497 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
26 Jun – 3 Jul
$223 NZD per night
Guest favourite
Cottage in Annapolis
4.96 out of 5 average rating, 332 reviewsRelaxing Water Views - Mill Creek Cottage
11–18 Jan
$429 NZD per night
Guest favourite
Boat in Annapolis
4.94 out of 5 average rating, 351 reviewsStay aboard the S/V MY STUDIO on Annapolis Harbor
2–9 Dec
$391 NZD per night
Guest favourite
Apartment in Annapolis
4.94 out of 5 average rating, 32 reviewsHillsmere Hideaway
16–23 Dec
$258 NZD per night
Guest favourite
Home in Arnold
5.0 out of 5 average rating, 36 reviewsPrivate Studio Getaway Near Annapolis
18–25 Apr
$250 NZD per night
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
28K reviews
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Condo rentals Annapolis
- Rentals with a fireplace Annapolis
- Rentals with lake access Annapolis
- Private suite rentals Annapolis
- Rentals with a washing machine and dryer Annapolis
- Rentals with a patio Annapolis
- Monthly Rentals Annapolis
- Waterfront rentals Annapolis
- Rentals with pools Annapolis
- Townhouse rentals Annapolis
- Kid-friendly rentals Annapolis
- House rentals Annapolis
- Rentals with outdoor seating Annapolis
- Rentals with a hot tub Annapolis
- Pet-friendly rentals Annapolis
- Rentals with an EV charger Annapolis
- Rentals with beach access Annapolis
- Fitness-friendly rentals Annapolis
- Apartment rentals Annapolis
- Family-friendly rentals Annapolis
- Rentals with breakfast Annapolis
- Rentals with a fire pit Annapolis
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom