Holiday Homes in Cumberland

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Featured Holiday Homes in Cumberland

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10.0 out of 10, Exceptional, (16)
"The house was beautiful and clean and in a great location (and smelled great too!). We arrived on Thanksgiving day and were pleasantly surprised to find a decorated Christmas tree lit by the fireplace. The house is a very convenient 10-15 minute drive to Oakland or McHenry. We loved sitting in the hot tub while it was snowing. Our granddaughter enjoyed the arcade game upstairs and was really excited about the bunk bed room. We had a wonderful stay and would love to come back in the warmer...
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

10.0 out of 10, Exceptional, (272)
"Our family rented Full Circle cottage in order to visit our daughter at WVU for a football game. It is about 45 minutes away. The cottage surpassed our expectations. It was spotless and the decor was Beautiful! The pictures did not do justice. The owners go above and beyond to make your stay special. Even cinnamon rolls in the freezer for the morning. The owner met us on arrival to show us around and made the beautiful, huge dining table. We had 10 people and more than enough room. I...
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

Lakefront/Dock/Amazing views HotTub

9.8 out of 10, Exceptional, (40)
"Great central location right off busy Garrett Highway. Nice amenities, could even suit 3 distinct groups with sleeping for 14. Walk out lower level directly to the lake, steps away. Nice hot tub, dock and kayaks. Fun game table and some arcade games if children come along. Enjoyable evening by the fire pit with s'mores! Easy to find, easy to book, responsive owners."
Lakefront/Dock/Amazing views HotTub

Deep Creek Lake Townhome w/ Deck & Water Views

9.6 out of 10, Exceptional, (32)
"Very clean and well maintained. Decor includes interesting items from around the world. Master bed was comfy, and owner was friendly on the phone. When she learned we were coming for my husband's birthday, she left a fun card for him with all the check-in info. We went in October and enjoyed the cozy gas fireplace and beautiful lake view. A busy road stands between the condo and the lake, but it's not a huge issue in cold weather when windows are closed. If you're looking for remote mountain...
Deep Creek Lake Townhome w/ Deck & Water Views

Ski-in/ski-out mountain-view home with hot tub, fireplace & year-round fun

9.0 out of 10, Wonderful, (52)
"This was a great fit for us. My son had his friends along so they had their own “space” in the lower level, and my daughter and I had plenty of room in the upstairs bedrooms. Nice kitchen and living area where we could all be together and the “kids” enjoyed the hot tub. The location was beautiful and “woodsy”. A few spiders joined us in the house, which was sort of expected anyhow. Was nice to have the washer/dryer on site. We loved the lake and surrounding sites. Definitely go see Muddy Creek...
Ski-in/ski-out mountain-view home with hot tub, fireplace & year-round fun

Beautiful Cabin in the Woods with Private Hot Tub & Game Room, Close to Skiing

9.6 out of 10, Exceptional, (73)
"Place is great! Family loved it! Great location close enough to eveeyrhing there is to do."
Beautiful Cabin in the Woods with Private Hot Tub & Game Room, Close to Skiing

Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK

9.4 out of 10, Exceptional, (30)
"Three nights in this property. Three levels. The place was very clean and had everything we needed. Thank you. "
Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK

Serene Mountain Escape: Hot Tub, Foosball, Views

9.6 out of 10, Exceptional, (4)
"House was very clean and well appointed. Nice location"
Serene Mountain Escape: Hot Tub, Foosball, Views

Level lakefront, family-friendly, hot tub, low fees, private dock

10.0 out of 10, Exceptional, (96)
"Enjoyed the house love you Can see the lake from "
Level lakefront, family-friendly, hot tub, low fees, private dock

Lake-view cabin with private hot tub, firepit & fireplace - dog-friendly

8.6 out of 10, Excellent, (18)
"This is a spacious vacation home that offered a good amount of privacy for both the adults and the teens in our party. The kitchen was well stocked as were the bedrooms and bathrooms. The neighborhood is quiet and situated along a large golf course. Access to the lake from the house takes a couple of minutes of walking and view of the lake from the house is limited due to mature trees and other homes. It takes about 10-15 minutes of driving to get to most stores and restaurants."
Lake-view cabin with private hot tub, firepit & fireplace - dog-friendly

Adventure retreat near ski lifts and lake - private hot tub, three balconies

8.6 out of 10, Excellent, (7)
"The townhouse itself is charming, impeccably maintained, and tastefully decorated. The updated bathrooms are a nice touch. During our stay over the July 4th weekend, the weather was hot, leading us (a family of 3) to sleep in the refinished basement as the second-floor bedrooms lacked air conditioning. However, the basement, complete with its own bathroom, sofa bed, bunk beds, smart TV, and a hot tub just outside, provided a comfortable and cool sleeping space. While there is a community dock...
Adventure retreat near ski lifts and lake - private hot tub, three balconies

Trail's End | 5 Bed, 3.5 Bath

2.0 star property
9.0 out of 10, Wonderful, (45)
"Most things were fine but we had planned barbecue get together with numerous people and the grill was not functioning. No response to request for compensation due to significant inconvenience. Had to find a way to barbecue elsewhere which was difficult with small children. That was to be our principal entertainment for the weekend."
Trail's End | 5 Bed, 3.5 Bath

Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.

10.0 out of 10, Exceptional, (87)
"Had a wonderful time at this ranch style lakeview home. Had all the amenities we needed! Host/0wner easy to communicate with a nicely priced! Highly recommend!!"
Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.

Lakefront Townhouse with Lake & Ski Access

7.2 out of 10, Good, (86)
"Overall everything is neat"
Lakefront Townhouse with Lake & Ski Access

Lakefront, dog friendly, dock slip, hot tub, and fire pit

10.0 out of 10, Exceptional, (34)
"Our family enjoys DCL every other year for Thanksgiving. This year, we stayed at Magnolia and we were not disappointed. The house was well stocked with every-thing we needed. We loved the different sitting arrangements that afforded all of us a place to escape from the chaos, when necessary. "
Lakefront, dog friendly, dock slip, hot tub, and fire pit

Grossi's Geschenk: Lake Access, Dogs Welcome, Dock Slip, Hot Tub, Fireplace!

8.6 out of 10, Excellent, (30)
"Accurate to the listing. Very nice cabin with all required amenities. Listing said no firewood provided but turned out to be leftover firewood available at property."
Grossi's Geschenk: Lake Access, Dogs Welcome, Dock Slip, Hot Tub, Fireplace!

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

8.4 out of 10, Very good, (26)
"Enjoyed our stay..location is great..close to restaurants and entertainment. "
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

Secluded & spacious retreat with private hot tub, carriage house & game room

9.6 out of 10, Exceptional, (46)
"Highly Recommend to rent, but not the sturdiest construction so I wouldn't buy one of the homes. Faucets were loose and/ or falling off. Still worked, but I did feel I was close to catastrophe..."
Secluded & spacious retreat with private hot tub, carriage house & game room

Dog-friendly cabin with firepit, deck, private hot tub, fireplace

9.8 out of 10, Exceptional, (15)
"Beautiful property for a relaxing weekend! Very cozy"
Dog-friendly cabin with firepit, deck, private hot tub, fireplace

Large Lakefront Home! Private dock and hot tub!

10.0 out of 10, Exceptional, (31)
"We had a great long weekend at Kookookachoo! The house was amazing and very clean. It was a beautiful property and there was so much to do! We would definitely go back!"
Large Lakefront Home! Private dock and hot tub!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Cumberland

Secluded, romantic cabin with hot tub on 12 acres of woodland.

10.0 out of 10, Exceptional, (80)
"This property was beautiful. Very clean and well maintained. Looks just like the pictures. It was a perfect getaway for us!"
The price is AU$540
includes taxes & fees
6 Jan - 7 Jan
Secluded, romantic cabin with hot tub on 12 acres of woodland.

Awesome New Property/ CANAL RIVER RETREAT

9.8 out of 10, Exceptional, (104)
"As always, we loved sharing our Thanksgiving holiday with family at this lovely house and home. The location along the Potomac River and C&O Canal towpath is fabulous, so close to town yet our own little world. The space is perfect for a large gathering, plenty of room for tables for the meal and for games afterward. Thanks for everything. "
Awesome New Property/ CANAL RIVER RETREAT

Charming Mountain View Retreat. Cozy place within walking distance to downtown.

8.8 out of 10, Excellent, (3)
"Property was clean, plenty of room and comfortable."
Charming Mountain View Retreat. Cozy place within walking distance to downtown.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.