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Ski-in/out vacation rentals in Cumberland County

Find and book unique ski-in/out homes on Airbnb

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Popular amenities for Cumberland County ski-in/out rentals

Ski-in/out house rentals

Home in Otisfield
4.7 out of 5 average rating, 10 reviews

Brand new family home 3BR Sleeps 8

BethAnnRating, 5 stars81 months ago
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!
Superhost
Home in Bridgton
4.8 out of 5 average rating, 15 reviews

Pleasant Mt. SLOPE SIDE Retreat!

ChrisRating, 5 stars2 months ago
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!
Guest favourite
Home in Bridgton
4.88 out of 5 average rating, 16 reviews

Elegant 6BR Home w/ extra 1BR loft Airbnb option

ScottRating, 5 stars7 months ago
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.
Guest favourite
Home in Bridgton
4.92 out of 5 average rating, 59 reviews

New England Lodge in Western Lakes Region of Maine

SteveRating, 5 stars6 months ago
Super pour les gros groupes
Guest favourite
Home in Oxford
4.98 out of 5 average rating, 48 reviews

Farmhouse at Oxbow Beer Garden

MorganRating, 5 stars2 months ago
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.
Guest favourite
Home in Bridgton
4.98 out of 5 average rating, 80 reviews

Easy Turns - Mountain Getaway

IvelinaRating, 5 stars7 months ago
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.
Home in Standish
4.25 out of 5 average rating, 12 reviews

Party’s , for large groups !Beach minutes

BethanyRating, 5 stars9 months ago
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! 🤗
Guest favourite
Home in Bridgton
5 out of 5 average rating, 5 reviews

The Ski Hive Trailside Pleasant Mnt

HaileyRating, 5 stars1 week ago
Andrea's Ski Hive was the perfect place for my large group and we couldn't be happier with the house and its listed amenities. Andrea was a communicative host and very clearly laid out all of our instructions and rules to follow.

Family-friendly, ski-in/out home rentals

Guest favourite
Home in Bridgton
4.92 out of 5 average rating, 59 reviews

New England Lodge in Western Lakes Region of Maine

SteveRating, 5 stars6 months ago
Super pour les gros groupes
Superhost
Condo in Bridgton
4.81 out of 5 average rating, 48 reviews

Pleasant Mountain Shawnee Peak Slope side condo

ErinRating, 5 stars2 months ago
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.
Townhouse in Bridgton
4.67 out of 5 average rating, 21 reviews

Luxury Pleasant Mountain Condo near Moose Pond

JennaRating, 5 stars14 months ago
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.
Superhost
Yurt in Durham
4.93 out of 5 average rating, 85 reviews

Hemlock Ridge Yurt at Maine Forest Yurts

JanetRating, 5 stars8 months ago
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!
Guest favourite
Yurt in Durham
4.93 out of 5 average rating, 123 reviews

Fisher Ridge Yurt at Maine Forest Yurts

BrienneRating, 5 stars7 months ago
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!
Home in Otisfield
4.7 out of 5 average rating, 10 reviews

Brand new family home 3BR Sleeps 8

BethAnnRating, 5 stars81 months ago
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!

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