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Ski-in/Ski-out holiday rentals in Bridgton

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

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Popular amenities for Bridgton ski-in/out rentals

Ski-in/out house rentals

Guest favourite
Home in Conway
5 out of 5 average rating, 6 reviews

Brand NEW Ski-in/Ski-out retreat at Cranmore Mt.!

WesleyRating, 5 stars1 week ago
House is fabulous at an amazing location. Super worth it!!
Top guest favourite
Home in Greenwood
5 out of 5 average rating, 26 reviews

Exquisite Rustic Modern Ski Haus| Bike Park Access

BriannaRating, 5 stars5 months ago
This house is beyond beautiful! Makes for the perfect weekend getaway. The built in speakers were a favorite! Can’t wait to come back.
Guest favourite
Home in Jackson
4.98 out of 5 average rating, 191 reviews

Mountain View Home | Steps to Hiking & Waterfalls!

BenjaminRating, 5 stars2 weeks ago
My wife and I had an amazing time with our 5 month old boy. This was our first family vacation with our son and we’ll remember it forever. This is a beautiful house with even more beautiful views! Everything was clean and tidy. You are only 7 minutes from Story Land and about 15 minutes from downtown North Conway making this the perfect location. We’ll definitely be booking with Brian again in the future!
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 Madison
4.96 out of 5 average rating, 24 reviews

Brand new Mountain Side Family Retreat

BiancaRating, 5 stars5 months ago
The house is perfect for a family with privacy in each room with a beautiful view and with many activities to do.
Guest favourite
Home in Newry
4.97 out of 5 average rating, 67 reviews

FUNHOUSE

IleneRating, 5 stars2 weeks ago
This was our second stay at the fun house, and we were reminded very quickly why we fell in love with it the first time. It truly feels like home while also nestled just steps away from the mountains. We had everything we needed for a family reunion to be full of love laughter and food. Thanks, Amanda for answering questions quickly and being a great host! We will be back!!
Superhost
Home in Bartlett
4.9 out of 5 average rating, 194 reviews

Fireplaced Mountain King Suite w/Hot Tubs & Pools

MeaganRating, 5 stars1 week ago
We had a wonderful time. It was a beautiful spot with access to many fun things to do for the family.
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.

Family-friendly, ski-in/out home rentals

Guest favourite
Home in Jackson
4.96 out of 5 average rating, 170 reviews

Jackson Chalet with great views

WendyRating, 5 stars2 months ago
This is our 2nd time staying here during winter break, and it checked all the boxes again this year. The place itself is super cute and cozy and just feels like home as soon as you walk in. The kids love having their own room downstairs and my son raves about the bed. In fact, he has me on a quest to recreate, as he puts it, "the bed situation" there. The upstairs living space is the perfect place to relax, and we spent time each day of our trip playing games while nestled in front of the fireplace. It's well positioned for easy access to Attitash and Wildcat as well as going into North Conway (Zebb's is always a must-do), but we also really love the town of Jackson. Going over the covered bridge feels like you're entering into a special tucked away place. Yesterday's restaurant has incredibly breakfast, Red Fox Inn has great dinner, and Nestlenook Farm is great for ice skating. If you're in the area, you also need to check out Vintage Baking Co. All around a great getaway!
Superhost
Apartment in Bartlett
4.87 out of 5 average rating, 297 reviews

Attitash Studio | 5min to Storyland| Pools

LaurenRating, 5 stars3 days ago
Anca was so responsive and very helpful with our stay. The space was great for our family of 4. We were close to the restaurants and entertainment North Conway offers. We wish we could have stayed longer!
Superhost
Home in Bartlett
4.82 out of 5 average rating, 72 reviews

The Mountain House

JillianRating, 5 stars1 month ago
The house is great - it accommodated our party of 12 (6 kids and 6adults) comfortably. It is steps aways from the slope which is so nice. If you plan to cook meals at the house I’d recommend packing cooking oils, seasonings, and food storage (aluminum foil, sandwich bags, etc) bc there are none of these items. There are also a limited number of pans. Otherwise the house is fantastic!
Superhost
Home in Intervale
4.83 out of 5 average rating, 334 reviews

Charming condo in white mountains, near Story Land

HiralalRating, 5 stars2 months ago
Inviting living room with beautiful mountain views. The bedrooms are spacious and well laid out. Great communication. We will plan staying here again.
Guest favourite
Apartment in Bartlett
4.92 out of 5 average rating, 455 reviews

Across from Storyland & in the Heart of the Mtns

CristenRating, 5 stars1 month ago
Highly recommend a stay at Michelle and Jason’s place! It’s a great “home base” for whatever you’re looking to do, whether that be hiking, climbing, skiing, shopping, or exploring any of the charming towns nearby! Michelle and Jason were kind and communicative and their place is so adorable and comfortable! Great stay!
Top guest favourite
Townhouse in Waterville Valley
4.98 out of 5 average rating, 61 reviews

Beautiful Sunny Townhouse Home

BrandonRating, 5 stars2 months ago
We had a wonderful stay at Lori’s condo with our two young children and another couple with their kids. The space was perfectly set up for our group, with plenty of room to spare. The condo’s location was ideal—right on the ski shuttle and within walking distance to the town square. It was cozy, comfortable, and the perfect base camp for a winter weekend filled with great memories. We’re so glad we found this booking and would definitely stay again!
Guest favourite
Flat in Gilford
4.89 out of 5 average rating, 347 reviews

Mountain View Cabin #1

JimRating, 5 stars1 month ago
Always a great stay at Jeff and Jayne's cabin. I think this was our 8th stay here and as always, a wonderful place to stay near Gunstock and Lake Winnipesauke.
Superhost
Apartment 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.

Ski-in/out cabin rentals

Cabin in Bridgton
4.75 out of 5 average rating, 4 reviews

Cozy slopeside 2 BR cottage perfect winter getaway

ChrisRating, 5 stars19 months ago
Cozy, comfy house in a beautiful location. Marilyn was very hospitable and responsive. We would definitely book again!
Cabin in Greenwood
4.95 out of 5 average rating, 40 reviews

Cabin w/ Views, Grill, Sauna, Pool Table, Games

AllaizaRating, 5 stars8 months ago
This place was ABSOLUTELY beautiful! It was very spacious and homey for group of friends. Would definitely recommend this place. Also if you’re planning on visiting during summer time, make sure you bring a fan to help regulate the temperature in your room especially for the room with the bunk beds. There was a ceiling fan in the living room and it helps a lot. We had a lot of fun in the basement with the pool table and darts. Overall we all had a great time and looking forward on staying here again!
Cabin in Bridgton
4.66 out of 5 average rating, 85 reviews

Mountaintop Cabin - Hike or Ski In!

LyndsayRating, 5 stars1 month ago
We book every year for a kid getaway and it’s always a good time!
Superhost
Cabin
4.64 out of 5 average rating, 116 reviews

Secluded getaway in White Mountains

CarynRating, 5 stars2 months ago
We've stayed here many times. It's rustic for sure, but that's what we want! The location is perfect and the house is peaceful and quiet. Kate and Arthur were very communicative and helpful.
Top guest favourite
Cabin in Greenwood
4.97 out of 5 average rating, 123 reviews

Cozy Cabin w/ Hot Tub & Fire Pit-Bike,Hike, Swim!

EricaRating, 5 stars2 weeks ago
This was a great stay, near many activities and restaurants. The view of the mountain was beautiful and the house was a perfect base for excursions. Carly was an excellent host and provided a wealth of useful information on things to do and see. I would definitely recommend this place to anyone.
Top guest favourite
Cabin in Gilford
4.98 out of 5 average rating, 249 reviews

The Lakes Region Log Cabin

CecileRating, 5 stars1 month ago
We had a week of event at the ski resort and the location was very convenient. The house was well described and furnished with all we needed. Sara and Christopher were super engaged and responsive hosts and gave us great recommendations for restaurants and places to check out.
Guest favourite
Cabin in Greenwood
4.95 out of 5 average rating, 20 reviews

Cozy Cabin, Big Views | Maine Mountain Retreat

DaneRating, 5 stars2 months ago
We had a lovely stay! The house was clean, roomy, comfy and had beautiful views of the nearby mountain range. Our host Kara was very responsive and accommodating throughout our stay. Would love to return again soon.

Quick stats about holiday rentals that are ski-in/out in Bridgton

  • Total rentals

    10 properties

  • Nightly prices starting at

    £60 before taxes and fees

  • Total number of reviews

    440 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Wifi availability

    10 properties include access to wifi

Destinations to explore