
Family-friendly holiday rentals in Greenwood
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Top-rated family-friendly rentals in Greenwood
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Family-friendly home rentals with a hot tub

★Spacious, Updated, Beautiful Condo @ The Seasons★
The condo was nicely stocked and had everything we needed for our family. Extra blankets in each closet and the beds were so comfortable! Easy to find and very close to the mountain we were skiing at for the week. Clubhouse with the pool was also within walking distance which was a huge plus.

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim
The house was beautiful. The walk down to the dock was also wonderful, the lake is beautiful. We really enjoyed the hot tub as well!

Best backyard in N Conway w/ hot tub, game room...
We spent a lovely few days at this property enjoying the winter weather at its finest. The house is close to everything but still felt private and cozy. A great choice for families!

Hot tub with country setting, close to village.
House was as listed, great location in a beautiful area. Plenty of amenities and host was helpful and responsive leading up to and during my stay.

"The GingerBread" 10 min from Sunday River!
Possibly the nicest Airbnb I’ve ever stayed in. This house was in spotless condition and looks even better than it does in the pictures. There’s a beautiful view from the back deck. It is the perfect place for a ski getaway and has so much character inside. From the hot tub to the pool table to the pinball machine, we were constantly having fun. Also didn’t have a single issue for the entire stay. 10/10.

Owl-Pine Ski Lodge: Rustic Cabin w/Hot Tub
The cabin was beautiful and spacious. Definitely can see all the updates and renovations that have been made. Rustic but with all the modern comforts. We were only there a couple of days but fit in an outdoor fire pit and hot tub! Wish we had a few more days off to enjoy more- but we made the most of it. I take any family time i can get! Thank you!

Blizzard Lodge
I had a wonderful stay at Julia’s place! From the moment I arrived, everything was exactly as described — clean, cozy, and thoughtfully prepared. Julia was a fantastic host: responsive, kind, and attentive to every detail, which made the whole experience smooth and enjoyable. The location was perfect, and the space felt like a true home away from home. I would absolutely stay here again and highly recommend it to anyone visiting the area. Thank you, Julia, for your hospitality!

A Large Vacation Home with hot tub, game room +
Very nice place. Great for a family getaway or a gathering with friends/couples. Most bedrooms have attached bathrooms which was great. Game room was very fun. Fooseball table is broken, so if you’re a rare foose junky like myself don’t plan on it. Only disappointment in this great home. Make sure to bring towels or you’ll be taking a trip to Walmart. Otherwise Highly recommend
Family- and pet-friendly home rentals

Tree House at the Shire
Our stay with at Christie and Richie’s treehouse was amazing! Not only were they exceptional hosts, but the accommodations were perfect. The treehouse is super cozy, the hiking trails are beautiful, and it’s all around peaceful place. We brought our dog and he had a great time as well! Their dog Bo was a great playmate for our dog. I highly recommend staying with Christie and Richie!

Large and lovely mountain cabin near North Conway
We had a great weekend with a blended family of young adults! There was hiking and visiting family also visiting while there! Great space and location!

Mountain View Retreat, Near skiing, shopping
We absolutely loved our stay! Plenty of room for 8 guests (and more!!) in a beautiful setting. There was many helpful amenities, like kitchen items, and plenty of towels. The location is perfectly centered to many popular things to do. James was always very responsive to questions left clear instructions. We highly recommend staying here and hope to do so again in the future.

Studio, pet friendly, river views, Jackson NH
Great place to stay for a weekend; the apartment was very clean and had many useful and thoughtful items in it (e.g. pots and pans, a coffee maker, extra toilet paper, dish/cleaning supplies, a hairdryer etc). We also appreciated that there were helpful little labels around the house and apartment for important light switches, the AC control vs the heat thermostat control, the hallway light, and the garage trash and recycle cans. The only thing we couldn't find and needed was a fly swatter; it's the tail-end of black fly season up north and we had to swat about 30 large flies right after arrival. One thing to note; this apartment is pet friendly, which was wonderful, but it is up a steep set of un-carpeted stairs. Our large dog found them slippery and it took a few tries before he was able to go up and down them without being afraid.

Classic Lakefront Maine Cabin
What a beautiful location! David is a great host. He made sure we had good directions, tips for the area, and was quick to answer any questions. The lakeside cabin has absolutely everything you need to have a peaceful, relaxing vacation. The view of the lake is spectacular. The cabin is very clean, has a well stocked kitchen, comfortable beds and Echo lake is a gorgeous pristine lake. Every morning, we enjoyed our coffee on the dock. We swam, kayaked, canoed and even tried out the paddle boards that came with the house. We would love to come back! Thanks!

Sunset Haven - Little Sebago Lake
We really enjoyed Elizabeth's house. It was beautiful and peaceful. The dock and beach were great. Communication was awesome! would loved to stay stay again.

The Banker's Suite
We had an excellent time during our stay. The location is walkable to restaurants and even hiking trails. There is a pottery store on the first floor (The Groggy Rabbit) we had a fun afternoon painting ceramics. The apartment is a LARGE one bedroom and plenty of space for our family of four with two young kids. Thank you Liz for a wonderful stay, we look forward to returning soon!

White Mt Retreat with New Kitchen and Beach Pass
The listing, the communication, the home, the location…all exceptional. Haven’t had a nicer place than this in a while. It was quiet and very comfortable. Minutes from great food, shopping, and things to love in the North Conway area. Very much recommended
Family-friendly home rentals with a pool

Upscale retreat w/ panoramic White Mountain views
We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

Attitash Studio | 5min to Storyland| Pools
Was a nice peaceful stay for the most part. The pools were nice to swim in although it seems not everyone seemed to want to follow the pool rules. Doesn't help that there were no lifeguards to ensure kids remained safe other than the parents. A few times I saw individuals in the pool water with either glass or an open drink in hand. Saw kids diving into the pool and even witnessed a few hurt themself. But other than that, the hot tub was so lovely to soak in. The arcade room was fun to play in. It was cool to see there was a lot to be able to do in the area for yourself. Definitely wish there was more to do in the area other than the classic tourists spots. A lot of beautiful spots to hike. We ended up checking out Diana's Bath and it was a gorgeous spot to watch cascading waterfalls or have a tiny dip. Would definitely check out this space again and maybe spend a few more days to truly appreciate the environment and mountains ^-^

Slopeside Sunday River Condo Brookside 2A210
Great place to stay with an awesome view of white heat!

Storyland, golf, hiking, kayak and more
We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

Attitash Retreat
This was our 2nd time staying at a unit hosted by ace on this resort and we will definitely return again! You get that private feel of a home with all the benefits of a hotel, not to mention beautiful Mountain Views when you step right out the door! Great location, 15 mins from Conway and we drove 30 min the other direction for the Mount Washington tour drive and we still wish we could’ve stayed longer. Our dog was more than welcome for a small pet fee. Highly recommend!!

Across from Storyland & in the Heart of the Mtns
Great stay! Very responsive host with awesome local recommendations that really made the trip. Would definitely come back!

Quiet Condo Close to Shopping and Attractions
Amazing place! Clean, lots of amenities, and the place had all the basics you could need! I will definitely be referring friends and returning for future trips!

Intimate Garden Style Condo with Mountain Views
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!
Quick stats about holiday rentals that are family-friendly in Greenwood
Total rentals
120 properties
Nightly prices starting at
₹6,910 before taxes and fees
Total number of reviews
4.5K reviews
Pet-friendly rentals
60 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
120 properties include access to wifi
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- Sebago Lake
- Sunday River Resort
- Story Land
- Attitash Mountain Resort
- Diana's Baths
- Mount Washington Cog Railway
- Fox Ridge Golf Club
- East End Beach
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Saddleback Ski Mountain Maine
- Cranmore Mountain Resort
- Purity Spring Resort
- King Pine Ski Area
- Wolfe's Neck Woods State Park
- White Lake State Park
- Omni Mount Washington Resort
- Sunday River Golf Club
- Portland Museum of Art
- Jackson Xc
- Bradbury Mountain State Park
- Wildcat Mountain
- Mount Prospect Ski Tow
- Conway Scenic Railroad