Ski-in/Ski-out vacation rentals in Cumberland County

5 out of 5 average rating, 17 reviews

A vibrant entryway showcases a door covered in a variety of stickers, creating a playful atmosphere. Hooks line the walls, adding functional charm, while natural light streams through the adjacent window. A welcome mat lies on the ground, enhancing the inviting entrance.

Apartment in Bridgton

Lil’ Ski Chalet-Private Assoc. Beach! 1 dog OK!

SaraRating, 5 stars1 month ago

We loved the proximity to the mountain for a little ski getaway and the amenities were excellent. This was definitely the best stocked Airbnb with anything you might need from yummy coffee and tea and any other kitchen amenity you can think of, cotton balls and q-tips in the bathroom, a night light, hand soap in the kitchen and the bathroom.... Plenty of hooks for coats by the door and extra hooks in the bathroom for towels. Plenty of indoor mats for leaving shoes by the door and a great sofa and tv for lounging. All in all we really appreciated the attention to detail to make our stay comfy and cozy!

A comfortable living area features a stone fireplace and large windows allowing natural light. Two plush sofas are positioned around an area rug, while a dining table is set nearby. Elegant decor elements and wood accents enhance the serene environment.

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!

4.98 out of 5 average rating, 48 reviews

A bright living area features exposed wooden beams and light-colored walls. Two comfortable sofas are arranged around a coffee table, with decorative cushions adding subtle detail. Natural light filters through multiple windows, creating an inviting space, while artworks hang on the walls.

Home in Oxford

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.

5 out of 5 average rating, 34 reviews

Ski equipment is displayed on a wooden chair alongside a vintage slot machine. A red Coca-Cola cooler can be seen in the background, adding a nostalgic touch to the space.

Chalet in Bridgton

April vacation open - great skiing still available

RaynaRating, 5 stars3 months ago

My family of 5 and I had a great time skiing between Christmas and the New Year at Pleasant Mountain. The home is spacious, fun, and comfortable. A standout amenity was the well stocked kitchen. We arrived very late after an extremely long drive and we were thrilled to find pancake mix, coffee, and other breakfast and lunch necessities for us to use! Our three children loved the basement rec room with ping pong/pool table and arcade games. Hosts were available via text to answer every question we had prior and during our stay. Would definitely recommend for future bookings!

The spacious exterior of the home is framed by lush greenery, with a wide porch showcasing seating areas. Sunlight filters through the trees, illuminating the well-manicured lawn. The house features a light yellow exterior and multiple windows, inviting a sense of openness.

4.88 out of 5 average rating, 16 reviews

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

ScottRating, 5 stars6 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.

5 out of 5 average rating, 12 reviews

A snow-covered landscape captures the serene beauty of the region, with cozy townhomes nestled among tall trees. Ski trails are visible, surrounded by a blanket of white. The distant mountains create a tranquil backdrop against a clear blue sky.

Chalet in Bridgton

Pleasant Mountain - Ski In and Out

KjRating, 5 stars2 months ago

Lee's Pleasant Mountain condo was the perfect get away for 4 nights on Pleasant Mountain for the 6 of us, (5 adults and a teen)! This condo is on the first line of condos on the far end away from the slopes. Even though it's a short walk to put on your skiis, it's still pretty great for a varied group of skiers who want to come and go as they please, or perfect for the guests who just want to curl up with a book or movie while the rest of the group hits the slopes till the lifts shut down! The bathrooms were all very clean, as was the kitchen and the bedrooms. The kitchen has everything you need to cook meals or mix cocktails. The bedrooms were especially comfortable! I don't think I've ever slept so well in a rental! (And that wasn't because of the long days of fresh powder skiing we were doing!) We'll definitely be back to stay next winter! Thanks Lee!

0 of 0 items showing

What guests are saying

Pleasant Mountain - Ski In and Out

5 out of 5 average rating, 12 reviews2 months ago

Lee's Pleasant Mountain condo was the perfect get away for 4 nights on Pleasant Mountain for the 6 of us, (5 adults and a teen)! This condo is on the first line of condos on the far end away from the slopes. Even though it's a short walk to put on your skiis, it's still pretty great for a varied group of skiers who want to come and go as they please, or perfect for the guests who just want to curl up with a book or movie while the rest of the group hits the slopes till the lifts shut down! The bathrooms were all very clean, as was the kitchen and the bedrooms. The kitchen has everything you need to cook meals or mix cocktails. The bedrooms were especially comfortable! I don't think I've ever slept so well in a rental! (And that wasn't because of the long days of fresh powder skiing we were doing!) We'll definitely be back to stay next winter! Thanks Lee!

Chalet in Bridgton

What guests are saying

Brunswick Farm Stay

4.99 out of 5 average rating, 87 reviews3 weeks ago

Seth and Maura provide a lovely, peaceful and spacious apartment with beautiful views to the outdoors. A perfect place to come back to after a busy day! I also very much appreciate their generosity and flexibility in accommodating a last minute change of plans. Thanks again for a great stay!

Farm stay in Brunswick

What guests are saying

Pleasant Mt. SLOPE SIDE Retreat!

4.8 out of 5 average rating, 15 reviews2 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!

Home in Bridgton

What guests are saying

Farmhouse at Oxbow Beer Garden

4.98 out of 5 average rating, 48 reviews2 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.

Home in Oxford

What guests are saying

Easy Turns - Mountain Getaway

4.98 out of 5 average rating, 80 reviews7 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 Bridgton

What guests are saying

Lil’ Ski Chalet-Private Assoc. Beach! 1 dog OK!

5 out of 5 average rating, 17 reviews1 month ago

We loved the proximity to the mountain for a little ski getaway and the amenities were excellent. This was definitely the best stocked Airbnb with anything you might need from yummy coffee and tea and any other kitchen amenity you can think of, cotton balls and q-tips in the bathroom, a night light, hand soap in the kitchen and the bathroom.... Plenty of hooks for coats by the door and extra hooks in the bathroom for towels. Plenty of indoor mats for leaving shoes by the door and a great sofa and tv for lounging. All in all we really appreciated the attention to detail to make our stay comfy and cozy!

Apartment in Bridgton

What guests are saying

Fisher Ridge Yurt at Maine Forest Yurts

4.93 out of 5 average rating, 123 reviews7 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!

Yurt in Durham

1 of 10 pages

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Cumberland County ski-in/ski-out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

A cozy living area features a stone fireplace framed by wooden paneling. Multiple seating options are arranged around a central coffee table, with a red couch and two beige sofas enhancing the space. Natural light is provided by windows adorned with blue checkered curtains.

4.92 out of 5 average rating, 59 reviews

New England Lodge in Western Lakes Region of Maine

Marc-AndréRating, 5 stars7 months ago

Thank you very much! Super.

4.98 out of 5 average rating, 48 reviews

Home in Oxford

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.

The entryway features warm wooden walls and two closed doors, one on each side. A window with a light-filtering shade allows natural light to enter, while a small potted plant sits on the windowsill. Ski equipment is neatly stored in the corner.

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.

A wooden dining table with four chairs is set beside a large window, providing a view of a snowy outdoor landscape. Brightly colored artwork adorns the walls, and a small plant is centered on the table. Light spills in, enhancing the warm ambiance.

Home in Otisfield

4.7 out of 5 average rating, 10 reviews

Brand new family home 3BR Sleeps 8

BethAnnRating, 5 stars80 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!

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!

4.88 out of 5 average rating, 16 reviews

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

ScottRating, 5 stars6 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.

A spacious living area is highlighted by a high, wooden ceiling and large windows, providing abundant natural light. A comfortable sectional couch, wooden coffee table, and stone fireplace create a welcoming gathering space. The adjacent kitchen area is visible, showcasing an open layout.

5 out of 5 average rating, 4 reviews

The Ski Hive Trailside Pleasant Mnt

LoriRating, 5 stars2 months ago

9 Adults and 5 children under the age of 4….plenty of space for all of us . The house is just beautiful and the ski in ski out made for the most perfect ski vacation…will definitely return!

A spacious living area features a gray sectional sofa with a variety of cushions in muted tones. A soft white rug lies on a light gray floor, while a wall-mounted air conditioning unit and artwork add character to the setting. The kitchen is visible in the background.

New place to stay

Mountainside

Show all

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

4.92 out of 5 average rating, 59 reviews

New England Lodge in Western Lakes Region of Maine

Marc-AndréRating, 5 stars7 months ago

Thank you very much! Super.

4.81 out of 5 average rating, 48 reviews

The image captures a row of rustic condos, characterized by wooden exteriors and peaked roofs. The setting features a rocky foreground and distant hills under a clear blue sky. Surrounding trees complement the natural landscape, enhancing the outdoor environment.

Condo in Bridgton

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.

A spacious living area is highlighted by a comfortable sectional sofa, inviting guests to relax. A stone fireplace sits in one corner, while large windows provide a view of the outdoors. A collection of games and books is stored on a nearby shelf.

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.

4.93 out of 5 average rating, 85 reviews

A spacious yurt is surrounded by tall trees in a wooded setting. A wooden picnic table is positioned nearby, along with a charcoal grill and a small storage shed. The yurt features a green exterior and a circular design, inviting a nature-filled experience.

Yurt in Durham

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!