Family-friendly holiday rentals in Westover

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Popular amenities for Westover family-friendly rentals

Family-friendly home rentals with a hot tub

Home in McHenry
4.88 out of 5 average rating, 16 reviews

Eagle's Rest | Close to Ski Slopes, Rafting + Golf

SeanRating, 5 stars1 month ago
The place was very nice! It was located in a gated community which was quiet and peaceful. The instructions to get into both the community and the house were very clear. All of the homes in the neighborhood were beautiful and well kept. The house exceeded our expectations and we would definitely stay there again. Taylor-Made was also very responsive with any questions we had before our stay and everything was easy to find in the house. Thank you for a great weekend!
Guest favourite
Cabin in Terra Alta
4.97 out of 5 average rating, 118 reviews

Rustic Memories/Near Deep Creek Lake/No extra fees

TomRating, 5 stars2 months ago
We stayed here for our 26th anniversary and it was perfect! It is an amazing cabin with incredible views. I highly recommend this cabin. The one piece of advice is because cell service is spotty don't trust your gps. Follow the instructions and look for the name of the cabin on the sign.
Home in McHenry
4.88 out of 5 average rating, 17 reviews

Canadian Day | Lake Access, 2 mi to Wisp Resort!

PeterRating, 5 stars10 months ago
This place was very nice. We liked the location. I will hit the highlights first: 1. Very nice rental property at the quiet end of the lake. 2. It was a mix of rustic outside and modern inside. 3. Very clean and comfortable on the inside, aside from a few spider webs (no big deal). 4. The hot tub was great 5. The staff were very responsive 6. Wood burning fireplace was great. Now the lowlights: 1. Driveway up to the property will make your toes curl the first time, but then you get used to it. 2. Lots of steps from the driveway up to the kitchen. 3. The dock is NOT convenient and you likely will not use it. Walking down to the dock is NOT horribly difficult (15 mins) downhill. However, the walk back was a challenge. 4. If you like to be cool when you sleep, pick the downstairs bedrooms. 5. The upstairs bedroom does NOT get cool, at all. 6. No real view of the lake from the house, maybe in the Fall? We will come back to DCL, however we will rent a lakefront property next time.
Guest favourite
Cabin in Terra Alta
4.94 out of 5 average rating, 78 reviews

(Bears Den) Near Deep Creek Lake (No extra Fees)

MadisonRating, 5 stars2 months ago
Beautiful place! Went on a girls trip and it fit exactly what we needed, cozy, nice views and relaxing. Only things I feel the need to make people aware of are that the hot tub is off the side of the house and you have to walk over gravel to get to it so bring flip flops, and that there are a TON of bugs in the house, we had ladybugs and stink bugs all over, fine for us but if it’s not something you can handle then bring traps. Overall amazing trip!
Superhost
Cabin in McHenry
4.85 out of 5 average rating, 33 reviews

Big Timber Retreat at Deep Creek Lake

ElizabethRating, 5 stars3 weeks ago
We had an awesome stay at Big Timber! We traveled with two families, including 5 kids - between the arcade, mini golf, fire pit and board games, our time passed so quickly and a great time was had! The place has a great authentic cabin feel, and it’s even better than the photos! Rick was easy to communicate with, and was always responsive. We will definitely try to return in the future!
Superhost
Chalet in Chalkhill
4.65 out of 5 average rating, 83 reviews

Vineyard View Chalet w/ Hot Tub!

DouglasRating, 5 stars6 months ago
Thanks David. If you ever are in need of a friend's getaway this is the place to go.
Home in McHenry
4.87 out of 5 average rating, 117 reviews

The Great Escape @ Deep Creek Lake

SapneshRating, 5 stars6 months ago
From the moment we stepped in, we were impressed by the thoughtfully designed interiors that radiated both warmth and elegance. The property truly exceeded our expectations. The spacious layout provided plenty of room for everyone to relax, while the play options for the kids were an absolute delight—they had such a great time! The well-appointed kitchen, with its clean and modern utilities, made cooking feel like a treat. Every detail was clearly curated with care and attention, creating an environment that felt inviting and luxurious at the same time. It added so much joy to our trip, and we’ll always treasure the memories we made here. We hope to return someday!
Guest favourite
Home in McHenry
5 out of 5 average rating, 10 reviews

Moonlight Ridge | Pet Friendly, Skiing, Activities

DesireeRating, 5 stars5 months ago
House was wonderful! Shout out to Emily at Taylor Made Rentals who went the extra mile for us to transfer to Moonlight Ridge. The house was cozy and just enough space to spend both quality time together and alone time when you need it! Kitchen was fully stocked with everyone to make a great meal and eat together at the large dining table. Our family felt right at home from the minute we arrived. We will heed the suggestions for an AWD vehicle next time but thanks to helpful folks in the area, we were able to make it out safely. Will definitely consider returning when the weather is warmer.

Family- and pet-friendly home rentals

Farm stay in Holbrook
4.88 out of 5 average rating, 136 reviews

-Red Onion Cabin @ Cole's Greene Acres (No Fees)

JessicaRating, 5 stars6 days ago
No words can say how wonderful Shane and Deanna's hospitality was. We had a large group that we were getting together for annual Father's Day weekend camping trip and at the last minute our accommodations fell through and we were scrambling to find somewhere that could host 20 people. the hosts at Cole's Green Acres were fantastic, very accommodating, and just overall an absolute delight. We were all super happy with the setup, especially since it rained tremendous amounts during the weekend we stayed. In fact, Shane even stated that this is the worst rain storms they've had in years! But we made it through and it was honestly so much fun hanging out underneath the Pavilion during the rain storms, watching the children run around playing in the rain, and then calming down at the fire pit just listening to music. To say that we loved our experience and appreciated the hospitality that Shane and Deanna provided would be an understatement. The amenities were more than listed! <3 you guys!
Guest favourite
Chalet in Confluence
4.92 out of 5 average rating, 222 reviews

Paddler's Lane Retreat - Riverside Chalet

BruceRating, 5 stars2 weeks ago
Chalet was a great getaway spot for a few days for an annual fishing trip. Every detail was perfect for us, had everything you could think of and thoroughly thought through the details to make sure you had all amenities needed. Grounds were also beautiful. People mention trains in their reviews but honestly didn’t mind it one bit, if you wanted they even had ear plugs in each room. Thanks again and our guide this week said he has had others stay there as well Bruce
Cabin in McHenry
4.85 out of 5 average rating, 171 reviews

Cozy Cabin in the Woods at Deep Creek Lake

EboniRating, 5 stars2 months ago
This listing was a great experience, everything we needed! The place was beautiful and everything was set up just fine. We had no worries. Highly recommended!
Guest favourite
Cabin in Confluence
4.86 out of 5 average rating, 72 reviews

Rustic Paradise - Ohiopyle is only 7 miles away!

Joseph T.Rating, 5 stars4 months ago
had a great stay at the cabin it was very clean and comforting. The fire place was great to sit in front of and watch a movie. its a easy place to find and get into; very quiet and great place to go on a hike just to relax. Thanks Joe
Guest favourite
Cabin in McHenry
5 out of 5 average rating, 14 reviews

Kaya Cabin on Deep Creek Lake

BillyRating, 5 stars1 week ago
Fantastic weekend getaway for two + our new puppy. Would recommend this cabin to anyone looking to stay near Deep Creek with furry friend(s)!
Chalet in Friendsville
4.83 out of 5 average rating, 86 reviews

Log Cabin overlooking the Yough River Valley

FranklinRating, 5 stars2 months ago
Our family of four and dog really enjoyed Tina and Robert’s Kendall Retreat. We stayed for 6 days and would have stayed longer if we could. Fun little area to explore, and their guidebooks are super helpful and spot on. The house was clean, space was perfect for us, and we loved enjoying the deck, fireplace, view and cooking in the beautiful kitchen. Ping pong and game system were added bonuses. Lots to do in the area in spring. Hiking, arcades/tracks, breweries, fun restaurants and also exploring the trails around the house. Would go back!
Superhost
Cottage in Ohiopyle
4.85 out of 5 average rating, 94 reviews

Family friendly cottage with hot tub in Ohiopyle!

DanRating, 5 stars9 months ago
The turning leaf lodge was a great place! It had a nice outdoor space for our family. Has enough room inside and out. I would recommend this place for anyone who wants to relax and enjoy some quiet time.
Cabin in Bruceton Mills
4.81 out of 5 average rating, 198 reviews

Broken Tractor Cabins: Rustic and Cozy.

SamanthaRating, 5 stars3 weeks ago
⭐⭐⭐⭐⭐ 5 STARS! Absolutely incredible property! Completely private, the absolute most private property we've ever been to! We had such a wonderful experience ☺️ We started our mornings hiking at Ohiopyle State Park and Cooper's Rock State Forest with the joy to come home to a wonderful property! The fire pit, walkable land and disc golf made for an excellent time to wind down. We are nature junkies and this place cannot get any better! Our pups were able to run freely and have literally the best time of their lives! The birds chirping and cows mooing made our experience even better. We strive to own a place like this in the future! Cannot wait to return next time we're in the area! Just a side note, currently there is no microwave, plan accordingly ☺️

Family-friendly home rentals with a pool

Superhost
Home in Ohiopyle
4.82 out of 5 average rating, 158 reviews

Walk to the Falls in Ohiopyle! Hot Tub,Fire Pit

JodiRating, 5 stars2 weeks ago
Ohiopyle is one of our favorite places! House was clean & comfortable. Provided almost everything we needed, Excellent attention to details. Awesome set up in the backyard, we all enjoyed very much!!
Home in McHenry
4.65 out of 5 average rating, 31 reviews

Mountain Top Lodge | Private Community Near Wisp!

TamerdisRating, 5 stars2 months ago
The experience was seamless and relaxing. The response time was impeccable. Highly recommend. My family enjoyed every second. Only drawback, we were a party of 7, the house holds a small water heater. After a few showers and washing, the hot water was cold, then needing to wait until the tank filled for hot water. This wasn’t even close to a deal breaker. We will be back many times over.
Top guest favourite
Cabin in Oakland
4.95 out of 5 average rating, 219 reviews

Private-Pool Access-Deck Fireplace & Hot Tub-XTRAS

BenRating, 5 stars1 month ago
Loved staying at Lazy Bear Lodge. Beautiful home with privacy on big property. Hosts were super responsive and gave great local recommendations. Very accessible to hiking and white water rafting.
Guest favourite
Cabin in McHenry
4.86 out of 5 average rating, 44 reviews

Cloud 10 at Deep Creek Lake

RachelRating, 5 stars4 months ago
The house had so much to do which was fantastic for our kids. They were happy to spend the whole day being entertained by the arcade, pool, and other amenities. Thanks!
Home in McHenry
4.62 out of 5 average rating, 21 reviews

Vista Bonita | Lake View, Community Pool!

RyanRating, 5 stars2 weeks ago
Great host, the house is beautiful inside and out. All guest enjoyed themselves and are already plans to go back in a few months.
Home in McHenry
4.88 out of 5 average rating, 16 reviews

Scenic Mountaintop Chalet w/ Hot Tub & Fire Pit

RickRating, 5 stars8 months ago
This house was awesome, cozy and warm, great view and location. We would come back here again. They did a great job decorating the home and it was very clean. One small issue, we were not able to get the direct tv to work for us. Had to pull things up on our computer and stream it through or watch Netflix. We didn’t watch it much. Also, the kitchen wall on the other side of the stairs (kitchen side) may need a fresh coat of paint. We really loved this home!!
Home in McHenry
4.75 out of 5 average rating, 4 reviews

Tao House | Hot Tub & Lake Access!

DonnaRating, 5 stars65 months ago
This cabin is beautiful and was perfect for our family weekend getaway. Very clean and great location. Wisp is less than five minutes away!
Chalet in Terra Alta
4.88 out of 5 average rating, 52 reviews

Lake View Chalet in Alpine Lake Resort

KaraRating, 5 stars9 months ago
Almost Heaven! Perfect home, perfect location for a family get-together. Bedrooms and bathrooms are comfortable and all needs will be met. The kitchen has everything you need to prepare meals. Just bring food! The lake is crystal clear and beautiful, and tall trees cover the landscape. The deer, chipmunks, squirrels and birds are right outside the door. The firepit was our evening spot to gather and chat. And toast marshmallows. And even though the kids are in their 40's, they made s'mores! This is a place to revive your soul. I could stay here forever.

Quick stats about holiday rentals that are family-friendly in Westover

  • Total rentals

    60 properties

  • Nightly prices starting at

    ₹2,596 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore