Holiday rentals in Annapolis
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Top-rated holiday rentals in Annapolis
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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
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
Guest favourite
Home in Annapolis
New Hotel Chic
Guest favourite
Guest suite in Edgewater
South River Park Apartment
Guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
Guest favourite
Guest suite in Annapolis
Great reviews! Pool, DT, stadium, goats, and more!
Guest favourite
Rental unit in Edgewater
Pet Friendly Garden Apartment Near Annapolis
Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Guest favourite
Rental unit in Annapolis
Eastport Bungalow
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
- Flat rentals Annapolis
- Townhouse rentals Annapolis
- Waterfront rentals Annapolis
- Apartment rentals Annapolis
- Rentals with a patio Annapolis
- Rentals with an EV charger Annapolis
- Pet-friendly rentals Annapolis
- Rentals with a fireplace Annapolis
- Rentals with outdoor seating Annapolis
- Fitness-friendly rentals Annapolis
- House rentals Annapolis
- Monthly Rentals Annapolis
- Rentals with a firepit Annapolis
- Family-friendly rentals Annapolis
- Rentals with a washing machine and dryer Annapolis
- Rentals with breakfast Annapolis
- Private suite rentals Annapolis
- Family-friendly rentals Annapolis
- Rentals with beach access Annapolis
- Rentals with a hot tub Annapolis
- Rentals with pools Annapolis
- Rentals with lake access Annapolis
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