
Ski-in/Ski-out vacation rentals in Cumberland County
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Cumberland County
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Cumberland County ski-in/ski-out rentals
Ski-in/ski-out house rentals

Brand new family home 3BR Sleeps 8
The house is amazing! Our daughter loved watching the chickens in the morning and we enjoyed sitting on the porch at night. We also enjoyed reading about the eco-friendly construction of the house. Very inspiring!

Cozy Knights Hill Home
We had a great stay at the house. Chris and Nadine were very responsive and helpful with information. The house is so comfortable in terms of layout and has everything you need. We enjoyed sitting by the fire and relaxing at the end of the day. Would highly recommend this home if you are staying in the area.

Pleasant Mt. SLOPE SIDE Retreat!
We were late booking a MA school vacation week trip and luckily found this place at the last minute. Perfect ski in/ski out location and excellent condo. Comfortable, well stocked, with an ideal layout. William and David were great to deal with. Couldn’t have asked for a better ski vaca with the family. We hope to stay again next year!

Elegant 6BR Home w/ extra 1BR loft Airbnb option
OMG The Manor at Boho Ridge was the perfect AirB&B for me and my friends for another friends son’s wedding near by. My friends were blown away at how beautiful this house is. The amenities, cleanliness & comfort that this house offers is second to none. I’ve been to a few AirB&B’s lately and this house was stocked beyond compare both in the kitchen & all the bathrooms. I probably don’t have to return to Maine anytime soon but if I did this would be the place I would choose. If you’re choosing a house in the area this is the one. Highly recommended for families or groups. We were 8 people and had room for at least 2 more if not 4 more.

New England Lodge in Western Lakes Region of Maine
Warm and very well-equipped cottage for groups.

Farmhouse at Oxbow Beer Garden
MAGIC. My husband spent a long weekend in the winter at this place and the property, house, and hosts were awesome. XC ski trails are right outside the front door. They were super well maintained and it was easy to rent equipment right on the property. The restaurant and beer garden is delicious. We ate there several nights and they have healthy options. The house had everything we needed including lots of linens and towels and extra blankets. The kitchen was well equipped. The hosts were super responsive via chat and very friendly. Looks like it would be really fun in summer but we had a great winter weekend.

Easy Turns - Mountain Getaway
We had a great time with the family at Laura’s place! Beautiful area, spacious house with everything needed. The fireplace was super nice in the cool nights and the game room was a nice entertainment. Private and surrounded by nature. Laura was very responsive and easy to communicate.

Party’s , for large groups !Beach minutes
Our bachelorette party of 14 guests fit comfortably in this space. This home is lovely and comfortable (it took me a bit to figure out the AC on day one, but after the first night the place got a lot cooler). Avigeya was extremely helpful and kind with communicating and making the space welcoming for us. We are all extremely satisfied with our experience staying at this house in Standish. Thank you! 🤗
Family-friendly, ski-in/ski-out home rentals

New England Lodge in Western Lakes Region of Maine
Warm and very well-equipped cottage for groups.

Pleasant Mountain Shawnee Peak Slope side condo
The ski in ski out at Pleasant Mountain is hard to beat for families. The hosts were super responsive and our party of 8 had a great time.

Hemlock Ridge Yurt at Maine Forest Yurts
We were exhausted but finally got to the yurt & it was incredible. Felt like 100 acres all to ourselves / our dog! We slept most of the time but the little exploring we did / our dog was just beautiful, quiet, relaxing!

Luxury Pleasant Mountain Condo near Moose Pond
We had a wonderful ski weekend with two families at the condo. It's a perfect location and very comfortable. We enjoyed all the games and toys provided for those who don't ski. The listing was as pictured and we felt at home right away.

Fisher Ridge Yurt at Maine Forest Yurts
This was our second time staying with Maine forest yurts. Last year we stayed at the zen den and this year at fisher ridge. Just like last year the yurt did not disappoint! We love the friendly hosts and the beautiful area in which the yurts are located. Fisher Ridge yurt is very clean and spacious. We enjoyed kayaking and fishing in the ponds! I even caught a pickerel! My first freshwater fish (after getting my Maine fishing permit of course)! Jess and I want to make our visit to the yurts an annual experience and I cannot wait for next year! Thank you again!

Brand new family home 3BR Sleeps 8
The house is amazing! Our daughter loved watching the chickens in the morning and we enjoyed sitting on the porch at night. We also enjoyed reading about the eco-friendly construction of the house. Very inspiring!

Moose Pond Mountain Escape
We had a lovely stay at James’ place! The hosts were very helpful and the area was beautiful. Would definitely recommend!
Ski-in/ski-out cabin rentals

Haggetts Haus
The perfect ski chalet! We stayed here for a family ski weekend at Pleasant Mountain and had such a wonderful time. The house is clean, cozy, comfortable, and SO close to the mountain! We couldn’t have asked for a better place to stay. The fireplace turns on with the click of a button, there is a basement entry for all the ski stuff, and the hosts were friendly and responsive. We definitely hope to make our stay at Haggetts Haus an annual tradition!

Cozy slopeside 2 BR cottage perfect winter getaway
Cozy, comfy house in a beautiful location. Marilyn was very hospitable and responsive. We would definitely book again!

Gorgeous Cabin minutes to Moose Pond & Lake Kezar!
Great home, great location, and a sweet little neighborhood. The house was cozy and inviting. We loved the 2 minute drive to the mountain for skiing.

Mountaintop Cabin - Hike or Ski In!
We book every year for a kid getaway and it’s always a good time!

Beautiful Campground by Sebago Lake!
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Story Land
- Attitash Mountain Resort
- Long Beach
- Surfside Beach
- Popham Beach State Park
- Long Sands Beach
- Fox Ridge Golf Club
- Cranmore Mountain Resort
- Pemaquid Beach
- Brunswick Golf Club
- East End Beach
- Palace Playland
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Purity Spring Resort
- King Pine Ski Area
- Parsons Beach
- Ogunquit Playhouse
- Bald Peak Colony Club
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