Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.
14–21 Feb
£187 per night
4.96 out of 5 average rating, 326 reviews
Guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill & fire bowl. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.
25 Mar – 1 AprIndividual Host,
£810 per night
5.0 out of 5 average rating, 103 reviews
Guest favourite
Cottage in Annapolis
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!
24–31 JulIndividual Host,
£160 per night
4.94 out of 5 average rating, 305 reviews

Popular amenities for Annapolis holiday rentals

Stay near Annapolis's top sights

Annapolis City Dock34 locals recommend
Navy-Marine Corps Memorial Stadium34 locals recommend
Graduate Annapolis11 locals recommend
Historic Inns of Annapolis8 locals recommend
Rams Head On Stage22 locals recommend
Boatyard Bar & Grill127 locals recommend

Other great holiday rentals in Annapolis

Guest favourite
Home in Annapolis
Sophisticated & Spacious Historic Home w/ Parking!
4–11 Nov
£528 per night
4.95 out of 5 average rating, 145 reviews
Guest favourite
Guest house in Glen Burnie
The Crab House - a Private, Waterfront Guest House
21–28 Sept
£207 per night
4.94 out of 5 average rating, 256 reviews
Guest favourite
Cottage in Annapolis
Charming Cottage - easy walk downtown with parking
2–9 DecIndividual Host,
£247 per night
4.92 out of 5 average rating, 144 reviews
Guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
23–30 Mar
£121 per night
4.96 out of 5 average rating, 50 reviews
Guest favourite
Flat in Annapolis
Eastport Bungalow
7–14 Apr
£127 per night
4.92 out of 5 average rating, 59 reviews
Guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
16–23 Nov
£330 per night
4.99 out of 5 average rating, 101 reviews
Guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
29 Nov – 6 Dec
£458 per night
5.0 out of 5 average rating, 81 reviews
Guest favourite
Flat in Annapolis
King George Hideaway
9–16 Dec
£159 per night
4.94 out of 5 average rating, 65 reviews
Guest favourite
Townhouse in Annapolis
Eastport Luxe in Annapolis
23 Feb – 2 Mar
£653 per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Annapolis
Green On Fleet - Rowhouse in Historic Annapolis
1–8 Nov
£253 per night
4.96 out of 5 average rating, 73 reviews
Guest favourite
Flat in Annapolis
WOW Downtown apartment w parking
18–25 AprIndividual Host,
£241 per night
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Annapolis
Boutique Historic Home Steps from the State House!
16–23 FebProfessional Host,
£553 per night
4.99 out of 5 average rating, 81 reviews

Quick stats about holiday 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

Destinations to explore