Guesthouse vacation rentals in Baltimore

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Top-rated guesthouses in Baltimore

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Guest favourite

Guesthouse in Annapolis

5 out of 5 average rating, 155 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.

Guest favourite

Guesthouse in Baltimore

4.87 out of 5 average rating, 205 reviews

Woodberry Studio Retreat

This newly constructed 600 sq. ft. studio loft features a contemporary open floor plan, full kitchen (new appliances), walk-in shower, yoga floor, big screen smart TV, queen bed, tons of morning and evening light, and is located in Historic Woodberry. This home is very private, safe, and fully equipped for short or long term stays. Walk to light rail station, JHU, Kennedy Krieger Institute, and the Hampden Avenue. Five star dining experience available just two blocks away, at Woodberry Kitchen.

Guest favourite

Guesthouse in Glenwood

4.95 out of 5 average rating, 181 reviews

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Guest favourite

Guesthouse in Annapolis

4.9 out of 5 average rating, 263 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.

Guest favourite

Guesthouse in Annapolis

4.87 out of 5 average rating, 353 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.

Guest favourite

Guesthouse in Annapolis

4.97 out of 5 average rating, 173 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.

Guest favourite

Guesthouse in Towson

4.99 out of 5 average rating, 220 reviews

Cute cottage studio with full kitchen and laundry

Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Guest favourite

Guesthouse in Highland

4.98 out of 5 average rating, 280 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

Superhost

Guesthouse in Glen Burnie

4.8 out of 5 average rating, 168 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.

Guest favourite

Guesthouse in Catonsville

4.97 out of 5 average rating, 244 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. It is not appropriate for people who cannot climb a ladder. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

Guest favourite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 322 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

Guest favourite

Guesthouse in Takoma Park

4.93 out of 5 average rating, 148 reviews

Newly renovated private rental - close to DC!

This space was just renovated and now has its own private bathroom on the same level! The above-ground rental has a full bathroom, queen size bed and kitchenette (small fridge, microwave and coffee maker) making sure you have the basics needed for exploring the area. Keyless access makes for easy check in. Located on a quiet residential street, you’ll get the rest you need for your time working or exploring the area.

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Baltimore guesthouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly guesthouses

Guest favourite

Guesthouse in Reisterstown

5 out of 5 average rating, 74 reviews

Cosy Highmeadow Cottage

Guesthouse in Annapolis

4.88 out of 5 average rating, 191 reviews

Annapolis Guesthouse - Completely Separate Space

Guest favourite

Guesthouse in Annapolis

4.94 out of 5 average rating, 98 reviews

Carriage House near Navy Stadium, parking, pets

Guest favourite

Guesthouse in Crownsville

4.98 out of 5 average rating, 63 reviews

The Studio on the Severn (Waterfront)

Superhost

Guesthouse in Crofton

4.64 out of 5 average rating, 121 reviews

Central location, Spacious, Private, More for less

Guest favourite

Guesthouse in Severna Park

4.98 out of 5 average rating, 83 reviews

Private Severn Riverfront Guest Cottage

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Guesthouses with a patio

Guest favourite

Guesthouse in Silver Spring

4.96 out of 5 average rating, 23 reviews

The Little Wooded Casita

Guest favourite

Guesthouse in Millersville

5 out of 5 average rating, 5 reviews

Newly Renovated 2b/1ba Unit

Guest favourite

Guesthouse in Arnold

4.88 out of 5 average rating, 16 reviews

Adorable 1 BR guest house with water views, deck

Superhost

Guesthouse in Silver Spring

4.67 out of 5 average rating, 9 reviews

Enchanting Backyard Tiny House, Bells & Whistles!

Guest favourite

Guesthouse in Downtown Silver Springs

4.91 out of 5 average rating, 47 reviews

Private guesthouse in heart of Silver Spring

Guest favourite

Guesthouse in Annapolis

5 out of 5 average rating, 11 reviews

Charming Rental in the Heart of Annapolis

Superhost

Guesthouse in Dayton

4.85 out of 5 average rating, 54 reviews

Cozy Cottage in Dayton

Superhost

Guesthouse in Hydes

New place to stay

The Cottage at Merryland Farm

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Guesthouse rentals with a washer and dryer

Guest favourite

Guesthouse in Northwest Washington

4.96 out of 5 average rating, 50 reviews

2 Bedroom Basement Suite - Rock Creek Park

Guest favourite

Guesthouse in Inner Harbor

4.84 out of 5 average rating, 50 reviews

Historic Apartment - Little Italy Charm

Guest favourite

Guesthouse in Spencerville

4.84 out of 5 average rating, 25 reviews

Adorable Guesthouse on Historic Farm.

Guesthouse in Ellicott City

4.79 out of 5 average rating, 43 reviews

Golden Rule of Ellicott City- USA

Guesthouse in Annapolis

New place to stay

Eastport Gem ~ Walk to Downtown Annapolis

Guest favourite

Guesthouse in Baltimore

4.89 out of 5 average rating, 28 reviews

The Birdhouse

Guesthouse in Baltimore

4.83 out of 5 average rating, 6 reviews

Modern Sunnyfield Guesthouse

Guest favourite

Guesthouse in Arnold

4.91 out of 5 average rating, 23 reviews

Magothy River Bay Cottage

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Quick stats about guesthouse rentals in Baltimore

Total rentals
20 properties
Total number of reviews
1.3K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
National Aquarium, Oriole Park at Camden Yards, and M&T Bank Stadium

Guesthouse vacation rentals in Baltimore

Top-rated guesthouses in Baltimore

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Baltimore guesthouses

Family-friendly guesthouses

Guesthouse in Reisterstown

Guesthouse in Annapolis

Guesthouse in Annapolis

Guesthouse in Crownsville

Guesthouse in Crofton

Guesthouse in Severna Park

Guesthouses with a patio

Guesthouse in Silver Spring

Guesthouse in Millersville

Guesthouse in Arnold

Guesthouse in Silver Spring

Guesthouse in Downtown Silver Springs

Guesthouse in Annapolis

Guesthouse in Dayton

Guesthouse in Hydes

Guesthouse rentals with a washer and dryer

Guesthouse in Northwest Washington

Guesthouse in Inner Harbor

Guesthouse in Spencerville

Guesthouse in Ellicott City

Guesthouse in Annapolis

Guesthouse in Baltimore

Guesthouse in Baltimore

Guesthouse in Arnold

Quick stats about guesthouse rentals in Baltimore

Total rentals

Total number of reviews

Rentals with dedicated workspaces

Wifi availability

Popular amenities

Local attractions

Destinations to explore