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

Guest house in Annapolis

4.9 out of 5 average rating, 202 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.

14–21 Nov

€ 112 per night
Guest favourite

Guest house in Annapolis

4.87 out of 5 average rating, 310 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.

7–14 Aug

€ 134 per night
Guest favourite

Guest house in Annapolis

4.97 out of 5 average rating, 152 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.

21–28 Jul

€ 154 per night

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
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

Cottage in Annapolis

4.94 out of 5 average rating, 307 reviews

Wright’s Cottage, Pets Welcome!

27 Jun – 4 Jul

€ 226 per night
Guest favourite

Guest suite in Arnold

4.94 out of 5 average rating, 110 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

3–10 Sep

€ 172 per night
Guest favourite

Apartment in Annapolis

4.96 out of 5 average rating, 144 reviews

The Crow's Nest - Excellent downtown Annapolis Apt

24–31 Aug

€ 193 per night
Guest favourite

Cottage in Annapolis

4.96 out of 5 average rating, 328 reviews

Relaxing Water Views - Mill Creek Cottage

21–28 Dec

€ 227 per night
Guest favourite

Guest suite in Annapolis

4.97 out of 5 average rating, 160 reviews

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

4–11 Nov

€ 166 per night
Guest favourite

Boat in Annapolis

4.94 out of 5 average rating, 349 reviews

Stay aboard the S/V MY STUDIO on Annapolis Harbor

6–13 Aug

€ 214 per night
Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 560 reviews

Old Bay Bungalow

22–29 May

€ 192 per night
Guest favourite

Apartment in Annapolis

4.96 out of 5 average rating, 51 reviews

Funky Uptown Apt meets Downtown - Hist District

15–22 Jun

€ 150 per night
Guest favourite

Guest suite in Annapolis

4.94 out of 5 average rating, 67 reviews

Annapolis Garden Suite

26 Apr – 3 May

€ 172 per night
Guest favourite

Guest suite in Riva

5.0 out of 5 average rating, 7 reviews

Cozy one bedroom appt on the water

17–24 Jul

€ 94 per night
Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 39 reviews

Naptown Suite

1–8 May

€ 109 per night
Guest favourite

Flat in Annapolis

4.92 out of 5 average rating, 59 reviews

Eastport Bungalow

27 Aug – 3 Sep

€ 175 per night

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