
Ski-in/Ski-out vacation rentals in Bridgton
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Top-rated ski-in/ski-out rentals in Bridgton
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Popular amenities for Bridgton ski-in/ski-out rentals
Ski-in/ski-out house rentals

Brand NEW Ski-in/Ski-out retreat at Cranmore Mt.!
House is fabulous at an amazing location. Super worth it!!

Exquisite Rustic Modern Ski Haus| Bike Park Access
This house is beyond beautiful! Makes for the perfect weekend getaway. The built in speakers were a favorite! Can’t wait to come back.

Mountain View Home | Steps to Hiking & Waterfalls!
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!

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!

Brand new Mountain Side Family Retreat
The house is perfect for a family with privacy in each room with a beautiful view and with many activities to do.

FUNHOUSE
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!!

Fireplaced Mountain King Suite w/Hot Tubs & Pools
We had a wonderful time. It was a beautiful spot with access to many fun things to do for the family.

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.
Family-friendly, ski-in/ski-out home rentals

Jackson Chalet with great views
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!

Attitash Studio | 5min to Storyland| Pools
My daughter and I really enjoyed this condo. The surroundings are so beautiful and it’s right up the road from North Conway and Diana’s Bath. Love the pool and hot tub on property. The flooring in the condo felt a bit dirty, like it wasn’t swept/mopped the best before our arrival but everything else was clean and tidy. Hosts were very responsive. Would stay again

The Mountain House
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!

Charming condo in white mountains, near Story Land
Inviting living room with beautiful mountain views. The bedrooms are spacious and well laid out. Great communication. We will plan staying here again.

Across from Storyland & in the Heart of the Mtns
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!

Beautiful Sunny Townhouse Home
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!

Mountain View Cabin #1
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.

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.
Ski-in/ski-out cabin rentals

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!

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

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

Secluded getaway in White Mountains
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.

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

The Lakes Region Log Cabin
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.

Cozy Cabin, Big Views | Maine Mountain Retreat
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 vacation rentals that are ski-in ski-out in Bridgton
Total rentals
10 properties
Nightly prices starting at
$80 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
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- Sebago Lake
- Squam Lake
- Scarborough Beach
- Sunday River Resort
- Loon Mountain Resort
- Attitash Mountain Resort
- Story Land
- Cranmore Mountain Resort
- Surfside Beach
- Owl's Nest Resort
- Fox Ridge Golf Club
- Wildcat Mountain
- Brunswick Golf Club
- Purity Spring Resort
- Franconia Notch State Park
- Cannon Mountain Ski Resort
- East End Beach
- King Pine Ski Area
- Mt. Abram
- Palace Playland
- Dunegrass Golf Club
- Sunday River Golf Club
- Omni Mount Washington Resort
- Bald Peak Colony Club
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