Vacation rentals in West Friendship

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Top-rated vacation rentals in West Friendship

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Top guest favorite
Guest suite in Woodstock
4.98 out of 5 average rating, 218 reviews

Our Retreat -in a peaceful setting.

Private- apartment in the lower level of our house. House in a rural setting- you may spot white tail deer or other wildlife.Enjoy the peaceful tranquil setting.We are within 5 minutes by car to Rte 70 and shopping centers. Our space isn't childproof. Workout equipment available for use at your own risk. We control the HVAC and will adjust as requested. May not be suitable for those with mobility issues due to the walk to the entrance. Non smoking. We aren't set up for heavy cooking. No stove.

Top guest favorite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis
4.96 out of 5 average rating, 456 reviews

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.

Guest favorite
A modern kitchen features a large island with bar seating and granite countertops. Stainless steel appliances and a six-burner gas range are present. Soft natural light filters through a window, illuminating a cozy living area with a comfortable sofa and decorative accents.
Guest suite in Glenelg
4.98 out of 5 average rating, 135 reviews

Lovely guest house with gourmet kitchen & King bed

If you're looking for a quick getaway or a brewery hopping good time we offer that and everything in-between. Locally offerings include walking trails/ restaurants, and family farms. We are located between Washington D.C. and Baltimore. Only a short 45 minute drive to D.C., you can spend the day exploring the museums and sites that the Nations Capital has to offer. Baltimore is 25 minutes away. A great place to see the National Aquarium. You will love your relaxing stay here in this rural area

Top guest favorite
A spacious gathering area is highlighted by a comfortable sofa and a light armchair, complemented by a brown coffee table. Wall art and mirrors add character to the gray walls. Soft rugs cover the wood-like flooring, creating a cozy atmosphere for relaxation.
Apartment in Sykesville
4.97 out of 5 average rating, 347 reviews

Heart of Sykesville! 2 Bedroom Suite! Walk to town

Located in the heart of Sykesville, Linden, a two bedroom basement suite, welcomes you to relax and rewind! We have designed our space to feel like your home away from home.The kitchenette includes a full refrigerator, microwave, slow cooker, Instapot, and a hot plate for meal prep. An easy stroll to Main Street will give your car a rest as you enjoy dining and shopping, live music from May/Oct and a wonderful Splash Park from May/Sept. Private guest patio with small gas grill. Dogs considered.

Guest favorite
Guesthouse in Glenwood
4.95 out of 5 average rating, 204 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.

Top guest favorite
Guesthouse in Ellicott City
4.92 out of 5 average rating, 103 reviews

Cozy Historic Guest House

Located in the heart of Old Ellicott City! This studio is warm, cozy and decorated with almost all vintage furnishings to pay tribute to the 1800s home. The space offers a well stocked bedroom, full bathroom and kitchenette. Relax on the patio or walk to the many cafes and shops on Main Street. Parking is included. The home is built into a hill so you will need to walk up a series of steps & stoned in the back from the parking area to enter. Due to this our home may not be ideal for everyone.

Guest favorite
The image depicts a small historic log cabin with white siding, surrounded by lush greenery and well-kept gardens. Nearby, a larger white building stands. The scene is set under a clear sky, with soft natural light illuminating the exterior.
Tiny home in Glenwood
4.89 out of 5 average rating, 159 reviews

Ellerslie cabin

Located in Glenwood, Maryland, Ellerslie is a 50 acre farm which dates back to 1763 with scenic views, fields of corn and a tranquil stocked pond. Nestled here is a small historic log cabin, built around 1810, that is charming and cozy. It has recently been restored and is equipped with all modern amenities, including a new stainless steel refrigerator and gas stove. The cabin is perfect for a business person who prefers staying in the country to a city setting or for a weekend getaway.

Top guest favorite
A bright and airy bedroom features a spacious bed with a white quilt and an accent pillow. Natural light filters through two windows, illuminating the wood floor. A small dining table with chairs and a wall-mounted air conditioner add functionality to the cozy space.
Guesthouse in Woodbine
4.95 out of 5 average rating, 147 reviews

Garden Cottage

Located in a beautiful and peaceful part of Maryland our Garden Cottage offers a cute and cozy getaway. A perfect escape from the city, our cottage is nestled among some of Maryland's best farmers markets, breweries, wineries, and outdoor experiences while still being conveniently located near several small towns and Frederick, MD. If you’re looking for a longer stay but our calendar looks booked please reach out to us!

Top guest favorite
A bright living area is presented, featuring a grey sofa adjacent to a rich brown ottoman. A small kitchenette is visible with a stove and refrigerator, complemented by open shelving. Natural light enters through a skylight and windows adorned with blinds. A doorway leads to a bathroom.
Guesthouse in Owings Mills
4.96 out of 5 average rating, 140 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Top guest favorite
Aerial view of a spacious cottage surrounded by lush green pastures and woodlands. The property features a large, circular driveway and open lawn areas, with fields stretching into the distance. The landscape showcases a blend of farmland and natural surroundings.
Farm stay in Damascus
5 out of 5 average rating, 122 reviews

Large countryside escape

Large, sparkling-clean, light-filled cottage with peaceful views of grazing horses, swaying pastures and mountains all around. Oversized dine-in kitchen and gathering room allow for reconnection. Clean linens, comfortable beds and quiet, allow for great rest. Unwind, reconnect and recharge in this magical place minutes away from the hustle and bustle of Damascus and 45 minutes from downtown DC.

Guest favorite
An outdoor seating area features two vibrant red chairs placed on a mulch bed. A small table stands between the chairs, surrounded by greenery and decorative plants. A bright red door provides an inviting entrance, while a vintage wrought iron fence encloses the area for privacy.
Guesthouse in Catonsville
4.95 out of 5 average rating, 336 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a thoughtfully designed eclectic modern retreat nestled beside our beautifully preserved 115-year-old Victorian home. Tucked along a peaceful, wooded path, this private cottage offers the perfect balance of charm, comfort, and convenience — ideal for couples, professionals, concertgoers, and travelers bringing their furry companions.

Guest favorite
The cottage features a welcoming exterior with a mix of orange and cream siding. Large windows allow natural light to fill the interior, while the front porch provides a shaded entry. A landscaped yard with trimmed shrubs surrounds the home, set against a backdrop of bare trees.
Cottage in Leesburg
4.93 out of 5 average rating, 288 reviews

The Cottage at Stone Tower Winery

The Cottage at Stone Tower Winery is a fully renovated, one-bedroom house located only an hour from DC, 30 minutes from Dulles Airport, and 15 minutes from Leesburg. The home is perfectly situated to enjoy a peaceful stay in the country and serves as an ideal location to explore the Northern Virginia wine region and historic Loudoun County.

Popular amenities for West Friendship vacation rentals