Guesthouse vacation rentals in Anne Arundel County

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Top-rated guesthouse rentals in Anne Arundel County

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

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Guest favorite

Guesthouse in Annapolis

5.0 out of 5 average rating, 139 reviews

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Nov 4 – 11

R5,158 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 207 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.

Oct 31 – Nov 7

R1,841 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.87 out of 5 average rating, 312 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.

Oct 2 – 9

R2,279 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 156 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.

Sep 25 – Oct 2

R2,744 ZAR per night

Guest favorite

Guesthouse in Bowie

4.85 out of 5 average rating, 67 reviews

Renovated Basement with Private Entrance

Fully renovated & updated basement with a full set of windows and sunlight. House is in a very nice and safe neighborhood. Walk-out basement with Private Entrance. Plenty of Parking. Non smoking. All Utilities and Wi-Fi are included. • Total Area: 800 Sq.ft. • One Bedroom with closet • Full Bathroom (Private) • Fully Furnished • Kitchen (Private) • Dining Area (Private) • Walk out Basement – Above ground (Private Entrance) • No Washer and Dryer • Plenty of Parking • No Smoking

Jun 5 – 12

R1,610 ZAR per night

Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Aug 11 – 18

R3,381 ZAR per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 208 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Sep 27 – Oct 4

R5,052 ZAR per night

Superhost

Guesthouse in Glen Burnie

4.81 out of 5 average rating, 155 reviews

Private 1 bedroom house

Just few miles away from Baltimore downtown, Ft Meade, NSA, Annapolis and Washington DC. Less than 5 miles away from BWI. It is detached one bedroom guest house with bedroom, full bathroom, kitchenette and living space. TV and WiFi !My place is good for couples, solo adventurers, business travelers, and pets. Private entrance, quite street, plenty of parking and close to everything! extra charge if you travel with pet - $25/pet. No parties.

Dec 24 – 31

R2,349 ZAR per night

Guest favorite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 263 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Dec 25 – Jan 1

R4,406 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Jun 13 – 20

R7,517 ZAR per night

Guest favorite

Guesthouse in Annapolis

5.0 out of 5 average rating, 106 reviews

Garden View, a spacious 1 bedroom with loft.

Take it easy at this unique and tranquil getaway located in a quiet neighborhood. Route 50, I-95, and Downtown Annapolis are all minutes away. Garden View is centrally located for Naval Academy sports, The Renaissance Festival, Boat Shows, and golf at The Preserve. Staying in? No problem, the kitchen is fully equipped, and with free wi-fi working at the desk is a breeze.

Jul 29 – Aug 5

R3,585 ZAR per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Recently renovated (Feb. 2021) one bedroom Guesthouse with fully equipped kitchen, new king sized bed with premium Saatva mattress, full bathroom and large living room in a quiet neighborhood near the South River, Quiet Waters Park and downtown historic Annapolis. We employ professional cleaning services between each guest stay.

Apr 12 – 19

R2,242 ZAR per night