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Family-friendly vacation rentals in Cumberland

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Top-rated family-friendly rentals in Cumberland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Guest favourite
Home in Cumberland
Jacob's Cottage
Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.
Jan. 13 – 20
$153 CAD per night
4.94 out of 5 average rating, 204 reviews
Guest favourite
Home in Cumberland
Charming 1907 Home in Historic Downtown Cumberland
This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with jacuzzi tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.
Apr. 4 – 11
$173 CAD per night
4.84 out of 5 average rating, 142 reviews
Guest favourite
Cabin in Frostburg
Big Savage Guest Cabin
Nestled on 10 acres near the summit of Big Savage Mountain is our home site which includes our two room guest cabin. Warm summer days and cool evenings make for a great vacation spot. Just one mile from downtown and the Allegheny Highlands Trail, your retreat is just 3 minutes from dining, biking, hiking, swimming, and live music. Fall brings beautiful foliage and winter plenty of snow. There is something for fans of all seasons. We are only 5 minutes from Frostburg State University.
Jul. 17 – 24
$168 CAD per night
4.92 out of 5 average rating, 132 reviews

Popular amenities for Cumberland family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cottage in Clearville
Grouseland's Vacation Cottage
May 6 – 13
$270 CAD per night
4.92 out of 5 average rating, 248 reviews
Guest favourite
Chalet in Great Cacapon
Fern Haven - Waterfront Chalet w/ WiFi & Hot tub!
Apr. 6 – 13
$367 CAD per night
4.94 out of 5 average rating, 365 reviews
Guest favourite
Cabin in Berkeley Springs
Horizon Hill - Log Cabin w/Hot Tub & Views!
Jan. 26 – Feb. 2
$367 CAD per night
4.93 out of 5 average rating, 459 reviews
Superhost
Cottage in Confluence
Magical Holiday Stream Side Cottage w/Hot Tub
Jun. 23 – 30
$541 CAD per night
4.83 out of 5 average rating, 121 reviews
Guest favourite
Cabin in Friendsville
The Crick House
Aug. 7 – 14
$235 CAD per night
4.97 out of 5 average rating, 275 reviews
Guest favourite
Cabin in Oakland
Winter is Coming
Dec. 18 – 25
$508 CAD per night
4.9 out of 5 average rating, 347 reviews
Guest favourite
Home in Oakland
Private&Cozy|HotTub|Firewood|CARC|Essentials|Sleds
Jan. 28 – Feb. 4
$844 CAD per night
4.95 out of 5 average rating, 189 reviews
Guest favourite
Cabin in Berkeley Springs
Private Modern Log Cabin w/Hot Tub
Apr. 26 – May 3
$400 CAD per night
4.91 out of 5 average rating, 135 reviews
Guest favourite
Home in Swanton
Log Cabin at the Lake, 5300+ sq ft of fun!
Jan. 31 – Feb. 7
$1,005 CAD per night
4.97 out of 5 average rating, 145 reviews
Guest favourite
Home in McHenry
Emerald Overlook, Deep Creek Lake
Jan. 8 – 15
$365 CAD per night
4.92 out of 5 average rating, 105 reviews
Superhost
Chalet in Accident
It's All Good @ Deep Creek Lake
Nov. 1 – 8
$450 CAD per night
4.81 out of 5 average rating, 134 reviews
Guest favourite
Home in McHenry
Ski/in Ski/out Luxury Home Voted #1
Sep. 29 – Oct. 6
$1,608 CAD per night
4.89 out of 5 average rating, 115 reviews

Family- and pet-friendly home rentals

Superhost
Cabin in Capon Bridge
WV Mountain cabin
Jul. 6 – 13
$201 CAD per night
4.78 out of 5 average rating, 306 reviews
Guest favourite
Cabin in Great Cacapon
Cozy Cabin on the Cacapon River
Apr. 8 – 15
$240 CAD per night
4.94 out of 5 average rating, 122 reviews
Guest favourite
Cottage in Normalville
Nice and Cozy Rental
Jan. 18 – 25
$228 CAD per night
4.93 out of 5 average rating, 440 reviews
Superhost
Cottage in Gerrardstown
Wooded Mountain Retreat near Creek
May 9 – 16
$153 CAD per night
4.85 out of 5 average rating, 277 reviews
Guest favourite
Cabin in Great Cacapon
Rustic Cabin on Cacapon River for Private Getaway
May 29 – Jun. 5
$161 CAD per night
4.91 out of 5 average rating, 234 reviews
Guest favourite
Cabin in Berkeley Springs
Retriever’s Retreat ~ High-Tech Log Cabin Oasis
Aug. 28 – Sep. 4
$301 CAD per night
4.83 out of 5 average rating, 179 reviews
Guest favourite
Home in Swanton
Alyvia's Retreat by the Lake (Lake Access)
Apr. 10 – 17
$424 CAD per night
4.95 out of 5 average rating, 211 reviews
Guest favourite
Home in Swanton
Lake Access Cabin, 3 private acres w/canoe, trails
Apr. 23 – 30
$352 CAD per night
4.85 out of 5 average rating, 327 reviews
Guest favourite
Home in Confluence
Paddler's Lane Retreat - Main House Rental - Full House
Feb. 8 – 15
$674 CAD per night
4.94 out of 5 average rating, 109 reviews
Superhost
Cabin in Capon Bridge
Potomac Cottage at Buffalo Gap Retreat
May 21 – 28
$276 CAD per night
4.87 out of 5 average rating, 110 reviews
Superhost
Cabin in McHenry
Cozy Cabin in the Woods at Deep Creek Lake
Dec. 16 – 23
$308 CAD per night
4.85 out of 5 average rating, 164 reviews
Guest favourite
Cottage in Oakland
Deep Creek Lake Cozy Cottage (Dog Friendly)
Apr. 28 – May 5
$615 CAD per night
5.0 out of 5 average rating, 88 reviews

Family-friendly home rentals with a pool

Superhost
Home in McHenry
Ski & Glee at Deep Creek Lake
Aug. 12 – 19
$1,385 CAD per night
4.91 out of 5 average rating, 34 reviews
Superhost
Cabin in Berkeley Springs
Hiking, WiFi, 4 Decks, King Suite, Community Pool
Aug. 22 – 29
$669 CAD per night
4.89 out of 5 average rating, 62 reviews
Guest favourite
Townhouse in McHenry
Top of Wisp Mountain, 5BR, Hot Tub, Theater, Gym
Feb. 1 – 8
$984 CAD per night
4.92 out of 5 average rating, 78 reviews
Guest favourite
Home in Swanton
5BR | Dock | Hot Tub | Fire Pit | Pool [castlelk]
Apr. 21 – 28
$1,237 CAD per night
5.0 out of 5 average rating, 5 reviews
Home in Swanton
Priv. Indoor Pool, Hot Tub, Free Golf&Mini,Tennis
May 12 – 19
$1,078 CAD per night
4.63 out of 5 average rating, 100 reviews
Home in McHenry
Glass Mountain Lodge | Private Hot Tub
Oct. 18 – 25
$670 CAD per night
4.71 out of 5 average rating, 7 reviews
Guest favourite
Cabin in McHenry
Cloud 10 at Deep Creek Lake
Sep. 13 – 20
$1,166 CAD per night
4.86 out of 5 average rating, 35 reviews
Guest favourite
Home in Berkeley Springs
Autumn Wings - A Natural Retreat
Jun. 22 – 29
$290 CAD per night
4.81 out of 5 average rating, 64 reviews
Guest favourite
Home in Berkeley Springs
Serendipity - Large 5BR with a Hot Tub
Jan. 23 – 30
$560 CAD per night
4.8 out of 5 average rating, 59 reviews
Superhost
Home in Berkeley Springs
Healing House - Healing Escape
Dec. 10 – 17
$386 CAD per night
4.76 out of 5 average rating, 25 reviews
Superhost
Home in Berkeley Springs
Almost Heaven - Cozy and Wonderful
Sep. 8 – 15
$315 CAD per night
4.74 out of 5 average rating, 19 reviews
Superhost
Home in Berkeley Springs
Black Forest - 5 Bedroom Escape
Feb. 6 – 13
$411 CAD per night
4.7 out of 5 average rating, 47 reviews

Quick stats about vacation rentals that are family-friendly in Cumberland

Total rentals

40 properties

Wifi availability

40 properties include access to wifi

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Total number of reviews

2.4K reviews

Nightly prices starting at

$68 CAD before taxes and fees

Destinations to explore