Vacation rentals in Annapolis

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Top-rated vacation rentals in Annapolis

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

Guest favourite

Guesthouse 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.

Nov. 14 – 21

$164 CAD per night
Guest favourite

Guesthouse 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.

Aug. 7 – 14

$196 CAD per night
Guest favourite

Guesthouse 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.

Jul. 21 – 28

$226 CAD per night

Popular amenities for Annapolis vacation 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 vacation rentals in Annapolis

Guest favourite

Cottage in Annapolis

4.94 out of 5 average rating, 308 reviews

Wright’s Cottage, Pets Welcome!

Jun. 27 – Jul. 4

$327 CAD per night
Guest favourite

Guest suite in Arnold

4.94 out of 5 average rating, 110 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Sep. 3 – 10

$252 CAD per night
Guest favourite

Condo in Annapolis

4.96 out of 5 average rating, 144 reviews

The Crow's Nest - Excellent downtown Annapolis Apt

Aug. 24 – 31

$284 CAD per night
Guest favourite

Cottage in Annapolis

4.96 out of 5 average rating, 328 reviews

Relaxing Water Views - Mill Creek Cottage

Dec. 21 – 28

$333 CAD 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

Nov. 4 – 11

$244 CAD 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

Aug. 6 – 13

$314 CAD per night
Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 560 reviews

Old Bay Bungalow

May 22 – 29

$282 CAD per night
Guest favourite

Condo in Annapolis

4.96 out of 5 average rating, 51 reviews

Funky Uptown Apt meets Downtown - Hist District

Jun. 15 – 22

$224 CAD per night
Guest favourite

Guest suite in Annapolis

4.94 out of 5 average rating, 67 reviews

Annapolis Garden Suite

Apr. 26 – May 3

$251 CAD per night
Guest favourite

Guest suite in Riva

5.0 out of 5 average rating, 7 reviews

Cozy one bedroom appt on the water

Jul. 17 – 24

$138 CAD per night
Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 39 reviews

Naptown Suite

May 1 – 8

$160 CAD per night
Guest favourite

Apartment in Annapolis

4.92 out of 5 average rating, 59 reviews

Eastport Bungalow

Aug. 27 – Sep. 3

$257 CAD per night

Quick stats about vacation 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