Cottage vacation rentals in Cumberland

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Quick stats about cottage rentals in Cumberland

  • Nightly prices starting at

    Cumberland vacation rentals start at ﺩ.ﺇ 624 per night before taxes and fees

  • Verified guest reviews

    Over 270 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cumberland rentals

  • 5 Average rating

    Cumberland stays are highly rated by guests—averaging 5 out of 5!

Top-rated cottage rentals in Cumberland

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

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Top guest favorite
An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.
Cottage in Winchester
4.99 out of 5 average rating, 473 reviews

COZY+SEXY Private Country Escape! HOT TUB & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Top guest favorite
A well-appointed kitchen features a central island with a marble countertop, surrounded by wooden cabinets and modern appliances. Natural light floods in through large windows, illuminating the dining area with a small table and four chairs. A patterned rug adds warmth to the wooden flooring.
Cottage in Berryville
4.99 out of 5 average rating, 158 reviews

Guest Cottage on Historic Estate & Cattle Farm

Fully restored c.1900 farm house on 190 acre estate, ~1 hr from D.C. Cottage is situated at end of a farm road (past the main house and barns), very private w/ creek and cows right outside. Enjoy walks on the farm, local hikes, breweries & wineries, pick-your-own fruit farms, tubing on the Shenandoah, restaurants, antique shops, and more. 1 queen bdrm and bath on 1st flr, 2nd queen bdrm & loft with twin beds on 2nd flr. wifi, fire pit, small grill. Over 25 only, Max 4 adults. 1 SMALL DOG ONLY.

Guest favorite
The exterior of a charming brown cottage is surrounded by lush green foliage. A spacious wooden deck with railing leads to the entrance, which is framed by white French doors. A red shade sail is positioned above the deck, adding a pop of color.
Cottage in Berkeley Springs
4.94 out of 5 average rating, 500 reviews

Hidden Hill - Cozy Downtown Cottage with Hot Tub!!

Hidden Hill is a renovated 1880’s cottage tucked away just above historic downtown Berkeley Springs. Xfinity high speed internet! Literally steps from spas, restaurants, art, antiques, and nightlife, this cottage also feels hidden just above downtown. Hidden Hill is a great spot to stay while enjoying everything Berkeley Springs has to offer. Explore everything West Virginia has to offer during the day, then retreat to Hidden Hill for the convenience of restaurants and bars at your doorstep.

Top guest favorite
A blue cottage is illuminated at night, showcasing distinct architectural features including gabled roofs and decorative trim. The background reveals a sprawling view of the city lights, creating a contrast against the dark sky. Trees and greenery frame the scene, enhancing the serene atmosphere.
Cottage in Cumberland
4.99 out of 5 average rating, 201 reviews

The Cottage on the Hill

Nestled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in one of your reserved spaces and step down to a unique retreat high above the city to enjoy a vintage cottage with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play pool, poker, board or yard games. Well appointed, fully equipped, and with a beautiful view, come relax and enjoy this one of a kind location.

Top guest favorite
A spacious outdoor area features a picnic table on green grass, with a fire pit surrounded by stone seating. The home is visible in the background, framed by tall trees and a clear blue sky, providing a serene country setting.
Cottage in Terra Alta
4.94 out of 5 average rating, 115 reviews

Country Charm/Near Deep Creek Lake/No Fees

Welcome to our Cranesville rental nestled in the pines and premiere farm land.We are just 12 miles from Deep Creek Lake where there are restaurants and Summer & Winter activities. 2 catch and release ponds. Sit next to the pond and let the massive pine whisper your stress away. There are cattle, sheep, horses, mules, and chickens for you to enjoy. (Gather fresh eggs for Breakfast) Enjoy nature while relaxing in this country farm setting. Firewood $5.00 a crate. 10 pieces in a crate.

Top guest favorite
The cottage exterior features a light-colored facade complemented by dark trim. A flag gently waves in the breeze, and surrounding lush greenery contributes to the tranquil setting. A gravel pathway leads to the entrance, creating an inviting access point.
Cottage in Hyndman
4.99 out of 5 average rating, 121 reviews

Mountain Oasis Cottage

Our Cottage is located at the base of a mountain on a dead end road it is very tranquil with a lot of deer that feed in the back yard. We are 15 minutes from the city of Cumberland Maryland where the “Western Maryland Bike Trail” is located and 30 minutes from historic Bedford, PA. The Cottage has two bedrooms that each feature queen size beds, one living room with a pull out queen size sofa bed, and a sitting room with a full size pull out sofa bed. Heated and cooled w/ mini splits.

Top guest favorite
The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.
Cottage in Green Spring
4.98 out of 5 average rating, 120 reviews

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

Top guest favorite
A cozy cottage is nestled among trees, featuring a spacious deck with chairs and a grill. A picnic table is situated on the lawn, providing ample outdoor seating. The surrounding greenery enhances the private and serene atmosphere of the property.
Cottage in Normalville
4.94 out of 5 average rating, 584 reviews

Nice and Cozy Rental

Great cottage nestled in the mountains on 63 wooded acres with barn, spring house and main house. Cottage has fireplace with first ring of logs provided. Two Smart TVs , VCR and DVD player with tapes and DVDs provided. Large deck and patio furniture off the living room with private woodland views and a babbling brook. Outdoor fire pit also provided. Close to Fallingwater, Ohiopyle and Seven Springs. Pet friendly (up to 2) and beautiful hiking trails in our woods.

Guest favorite
An outdoor area features a black gazebo with flowing curtains, providing shade for a seating area. A dining set is positioned under an umbrella, while steps lead down to a landscaped space with neutral stone accents and plants, enhancing the tranquil setting.
Cottage in Normalville
4.96 out of 5 average rating, 179 reviews

Entire Cottage w/ Additional Creek Cabin

****Please read entire description of property*** Main cottage (available year-round) - 1 bedroom, 1 sleep sofa in living room, 1 full bath, 1 half bath off kitchen Additional creek-side cabin (only available April 1- November 1 - $85/night plus $50 cleaning fee) - 1 bedroom, sofa, 1 full bath, dry kitchenette We never rent the creek-side cabin separately from the main cottage. If you do not need to rent it, you will still have access to the creek-side deck.

Guest favorite
A rustic cottage is showcased within a wooded setting, featuring a welcoming front porch with wooden railings. An American flag hangs beside the door, while decorative skis are mounted on the facade. A gravel driveway leads to a nearby garage.
Cottage in Swanton
4.92 out of 5 average rating, 283 reviews

*Deep Retreat* Fenced Dog Yard-Hot Tub-Fire Pit

Deep Retreat Cottage is 10 minutes from Wisp resort and most Lake activities! Boat Slip, Fire Place, Hot tub, fire pit, wifi and Streaming smart hdtv's. Awesome outdoor area with corn hole and horse shoes. The Cottage is Comfy, Cozy and ready for your Deep Creek Lake getaway. 2 Bedroom, 2 bath with loft sleeps 8 adults comfortably with amenities including Fire Place, Hot Tub, Fire Pit, WIFI and Gas and Charcoal Grills. Minimum Rental Age - 25

Top guest favorite
Two black rocking chairs are positioned on a stone patio, each adorned with a decorative pillow. A wide window provides views into the interior, framed by a white picket fence in the background, enhancing the outdoor sitting area.
Cottage in Oakland
4.96 out of 5 average rating, 200 reviews

Stone Haven

Welcome to Stone Haven — a cheerful stone cottage just minutes from Deep Creek Lake. Guests love Stone Haven for its charm, cleanliness, thoughtful touches, cozy atmosphere, and convenient location near the lake, Wisp Resort, hiking trails, restaurants, and local shops. Whether you’re visiting for lake days, skiing, hiking, or a quiet weekend away, Stone Haven offers a relaxing and comfortable place to return to after exploring the area.

Superhost
A hot tub is situated under a wooden pergola, with bubbling water visible. Nearby, a fire pit is surrounded by seating, and a grassy yard stretches out towards a cozy cabin. String lights hang above, creating a welcoming outdoor space.
Cottage in Mill Run
4.86 out of 5 average rating, 210 reviews

Cozy Ohiopyle/Fallingwater Cabin Hot Tub Fire Pit

OHIOPYLE< SEVEN SPRINGS<FALLINGWATER<STATE GAME LANDS*** Ski, Bike, Hike, Sled, Hunt, Fish -1.5 miles to OHIOPYLE , 20 minutes to SEVEN SPRINGS!!!! Perfect for a couples retreat or weekend with friends. Cute and cozy for a fun getaway. Outdoor fire pit. Fully equipped kitchen. Location>Location>Location!! Winter specials available! Linens and towels provided. 5 minutes to Fallingwater 2 minutes to rafting, hiking and biking

Popular amenities for Cumberland cottage rentals

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  3. Maryland
  4. Allegany County
  5. Cumberland
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