Cottage vacation rentals in Cumberland

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Top-rated cottage rentals in Cumberland

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Superhost

Cottage in Berkeley Springs

4.73 out of 5 average rating, 60 reviews

Blue Skies Ahead: Charming 3 bdrm Cottage w/patio

Our charming 3-bedroom cottage has everything you need for your Berkeley Springs trip. The home comes with fast Wi-Fi and self check-in. It backs to woods for privacy and views of the local wildlife. Visit the quaint shops and medicinal springs at the Berkeley Springs State Park or book a massage! Our home boasts 1.5 baths, a full newly renovated kitchen and washer/dryer. It is within driving distance to several popular museums, hikes, and cafes. An ideal base to explore Berkeley Springs.

Guest favorite

Cottage in Berkeley Springs

4.95 out of 5 average rating, 442 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.

Guest favorite

Cottage in Hyndman

4.99 out of 5 average rating, 106 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 and wildlife 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. We also have central air!!

Top guest favorite

Cottage in Capon Bridge

5 out of 5 average rating, 26 reviews

*New* River Front Retreat *HotTub-FirePit-Kayak*

Hummingbird Hideaway a River Front Cottage is the perfect place to relax & recharge. *Steps from the cleanest river in WV *Hot tub with river views *Kayaks on property, launch right off property *Decks with BBQ and dining Alfresco *Two Fire pits: River Front Wood Fire pit and Propane on the Deck *Yard games and board games *Wi-Fi and Smart TV. *Pet-Friendly This is a place where time slows down and the soul finds rest. Come step into nature and nurture your spirit at our riverfront haven.

Guest favorite

Cottage in Cumberland

4.99 out of 5 average rating, 182 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

Cottage in Winchester

4.94 out of 5 average rating, 36 reviews

Modern 3BR country farmhouse

Welcome to our home in a quaint country village outside of Winchester, VA. We have the best of both worlds: historic charm and modern living. The kitchen is well appointed and ready for you to create great meals to enjoy on our two porches or beside the fireplace. Master bedroom is en suite with double sinks. Relax on the porch swing listening to the sounds of the countryside. The fire pit is ready for s’mores! Veteran owned property. **New for 2025- Game room open!**

Superhost

Cottage in Oakland

4.98 out of 5 average rating, 97 reviews

Deep Creek Lake Cozy Cottage (Dog Friendly)

Bright, light, newly renovated lake cottage situated on a wooded lot, with cozy fireplace, large deck areas-front and back (with gas firepit), and 3 bedrooms with french doors that open to outdoor space. Community lakefront with private lake frontage just a short walk away. Enjoy swimming and water sports from the dock and lakefront area, snow skiing, sledding, tubing and snowboarding at Wisp Resort, hiking, Swallow Falls State Park and Deep Creek Lake State Park.

Guest favorite

Cottage in McHenry

4.97 out of 5 average rating, 61 reviews

Making Memories at the Lake

This cozy cottage is lake-front, within walking distance to ski slopes!! Just a short drive from numerous restaurants and cafes, nightlife spots, adventure filled activities, shopping, movies, and golf. Guests will have access to a kayak, canoe, charcoal grill, picnic table (in storage area) and fire pit. Inside, the home is comfortable, board games and puzzles are available. Family room has a new 42” TV, master bedroom also has a TV, WiFi is provided.

Guest favorite

Cottage in Oakland

4.94 out of 5 average rating, 218 reviews

Pet-Friendly Cozy Home w/Hot Tub & Fire Pit

Wisp Away to this lovely cozy home. Located walking distance from Deep Creek Lake and only a short drive to Wisp Resort. Centrally located near all the area's amenities including parks, restaurants, golfing, boating, beaches and so much more. This home features a queen-sized bed, a full bathroom, and a kitchenette. Relax at home by the firepit or soaking in the hot tub. Pets are welcome. We look forward to sharing our cabin with you and your fur baby.

Top guest favorite

Cottage in Oakland

4.95 out of 5 average rating, 127 reviews

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

Top guest favorite

Cottage in Berkeley Springs

4.95 out of 5 average rating, 144 reviews

Cozy Cottage in the heart of Berkeley Springs WV

Welcome to Elizabeth Cottage in honor of our Queen HRH Elizabeth II. Our spacious 3 bedroom cottage will make you feel right at home in the historic town of Berkeley springs! We welcome all pets and have a fully fenced in yard and screened in porch for them to enjoy! We are walking distance from our small town shops, and restaurants! >British Cottage Style >55" TV w/ roku streambar >Xfiniti Wifi >Hot tub, Fire pit, Grill ** No Cleaning Fee **

Top guest favorite

Cottage in Swanton

4.93 out of 5 average rating, 28 reviews

Lakefront Cottage with Spectacular Views

Lakefront cottage with tremendous views and private dock . Home is on a quiet lane with pedestrian friendly activity. This is an original lakefront cottage that has been completely updated. Swim or fish from the dock or shoreline, bring your own boat, or use the two sea kayaks provided. Well equipped kitchen. Quaint, updated cabin offers relaxing atmosphere, serene family environment. No large groups or partiers allowed.