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Pleasant Ridge Vacation Rentals

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Dec 5 - Dec 6
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Dec 6 - Dec 7
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Pleasant Ridge

Exterior
Sugarloaf camp - ski/ outdoors rustic retreat

Cabin in Carrabassett valley

10.0 out of 10, Exceptional, (14)
"It was close to my work and a good place to stay "
United States
Johnnie B.
Sugarloaf camp - ski/ outdoors rustic retreat
Exterior
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

Cottage in Strong

9.4 out of 10, Exceptional, (137)
"Very relaxing!"
United States
Bradford B.
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Property grounds
Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf

Cabin in Highland Plantation

10.0 out of 10, Exceptional, (106)
"Great place, just what we needed, and great hosts."
United States
Michael S.
$150 nightly
The price is $164
Dec 7 - Dec 8
Total with taxes and fees
Quiet rural Maine cabin near Bigelow Preserve, Flagstaff Lake and Sugarloaf
1 bedroom, WiFi, bed sheets
One Bedroom Ski-In/Ski-Out Condo on Whiffletree Chairlift. Short Walk to Village

Condo in Carrabassett Valley

2.0 star property
One Bedroom Ski-In/Ski-Out Condo on Whiffletree Chairlift. Short Walk to Village
TV, books
Mountain-View Deck! Cabin By Mt Abraham Skiing

Cabin in Salem Township

2.0 star property
Mountain-View Deck! Cabin By Mt Abraham Skiing
Property grounds
Sugarloaf West Mountain Summit Lodge

Vacation Home in Sugarloaf

9.4 out of 10, Exceptional, (48)
"This was the second time I've stayed at Jill's with my family and we had a great time! Plenty of space for our group!"
United States
Kailey H.
$1,188 nightly
The price is $1,295
Dec 7 - Dec 8
Total with taxes and fees
Sugarloaf West Mountain Summit Lodge
Dining
Awesome house in Kennebec Valley. Dog Friendly! OUTDOOR FUN! w-Wifi!

Vacation Home in Caratunk

2.0 star property
9.6 out of 10, Exceptional, (21)
"Plenty of space, clean. Great stay"
United States
Lindsey P.
Awesome house in Kennebec Valley. Dog Friendly! OUTDOOR FUN! w-Wifi!
Interior
Gorgeous dog-friendly cabin with great view, deck, hot tub, & gas fireplace

Cabin in Carrabassett Valley

9.8 out of 10, Exceptional, (14)
"Property was excellent. The check in / out process was smooth and easy. The main living area was well set up. We spent a great deal of time chatting around the bar and table in the open concept set up, as well as on the spacious deck. The hot tub was the best one we've encountered in our travels, my group of golfer particularly enjoyed its foot massager function! There were plenty of beds and all were comfortable. We would definitely book this location again and have shared it with friends for...
United States
Anonymous traveler
Gorgeous dog-friendly cabin with great view, deck, hot tub, & gas fireplace
5 bedrooms, iron/ironing board, WiFi
Carrabassett River Retreat

Vacation Home in Kingfield

10.0 out of 10, Exceptional, (4)
"Cozy, comfortable, easy access to huts-and-trails and Sugarloaf. Beautiful property. Excellent host."
United States
Cathy E.
Carrabassett River Retreat
Exterior
On Mountain Home, Spectacular Mountain Views, Ski to the Door

Vacation Home in Carrabassett Valley

10.0 out of 10, Exceptional, (71)
"Great location for a family summer vacation. "
United States
Sarah M.
On Mountain Home, Spectacular Mountain Views, Ski to the Door
Exterior
Dog-friendly chalet + hot tub, EV charger

Chalet in Carrabassett Valley

10.0 out of 10, Exceptional, (17)
"We had a great early Spring stay at Loafer’s Lodge - well appointed, comfortable and clean. The decks and hot tub were especially nice and the house has everything we needed. Thanks for a great stay"
United States
Carolyn M.
Dog-friendly chalet + hot tub, EV charger
Property grounds
Spacious Riverside Cabin Near Sugarloaf – Perfect for Family Getaways

Vacation Home in Kingfield

9.6 out of 10, Exceptional, (53)
"Fantastic place"
United States
Andrew M.
Spacious Riverside Cabin Near Sugarloaf – Perfect for Family Getaways
2 bedrooms, iron/ironing board, travel crib, WiFi
Luxury Ski-In/Out Condo at Whiffletree SuperQuad

Condo in Carrabassett Valley

10.0 out of 10, Exceptional, (2)
"Our stay here was wonderful. The condo is very spacious, clean, organized and had everything we needed and then some. Steps to whiffletree made taking the scenic lift ride easy. We were able to just walk to the base lodge and all surrounding restaurants on mountain. Perfect location! Beautiful space. We will definitely be back."
United States
Ashley P.
$969 nightly
The price is $1,056
Dec 7 - Dec 8
Total with taxes and fees
Luxury Ski-In/Out Condo at Whiffletree SuperQuad
Standard Cabin, 2 Bedrooms, River View | Individually furnished, bed sheets
Kennebec Riverside Cabins

Cabin in West Forks

2.0 star property
7.2 out of 10, Good, (5)
"The cabins were located right on the river with amazing view peaceful and quiet. What a great place to stay too get away from all the hustle and bustle 0f big city’s. "
United States
Dan
Kennebec Riverside Cabins
Fridge, microwave, oven, stovetop
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

Vacation Home in Madison

9.6 out of 10, Exceptional, (72)
"Such a cute home with lots of personality and "
United States
Heidi F.
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Smart TV
Dog-friendly cabin - Built in 2022!

Cabin in Carrabassett Valley

9.6 out of 10, Exceptional, (12)
"The property was great, plenty of room and super clean. Close to mountain."
United States
lisa e.
Dog-friendly cabin - Built in 2022!
Fireplace
Ski Camp - Sugarloaf

Cabin in Kingfield

Ski Camp - Sugarloaf
Interior
Expansive Getaway with Mountain Views, Hot Tub, Home Theater & Game Room

Vacation Home in Carrabassett Valley

8.8 out of 10, Excellent, (17)
"Lovely home and location!"
United States
Owen W.
Expansive Getaway with Mountain Views, Hot Tub, Home Theater & Game Room
Interior
The Epic Sugarloaf Getaway

Chalet in Carrabassett Valley

10.0 out of 10, Exceptional, (1)
"Just one suggestion, in the listing it appears as if there are 4 bunk beds, but it is 2 bunk beds.Nothing but good things to say about this property and the host/manager. Thank you very much!!"
United States
Matteo B.
$745 nightly
The price is $812
Dec 7 - Dec 8
Total with taxes and fees
The Epic Sugarloaf Getaway
Fridge, microwave, oven, stovetop
Welcome Outdoor Enthusiasts! Atv and snowmobile access

Vacation Home in Bingham

10.0 out of 10, Exceptional, (27)
"Great place to stay for access to the ATV trails. Hopefully we will be back soon."
United States
Jason F.
Welcome Outdoor Enthusiasts! Atv and snowmobile access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pleasant Ridge Hotel Reviews

Sugarloaf Mountain Hotel

Sugarloaf Mountain Hotel

10/10 Excellent
"Nice rooms, ski locker, excessively salty tofu eggs but nice vegan option at 44 restaurant No large towels in spa or hot tub Inconsistencies in staff knowledge on ski conditions or openings of beginners slopes "
Wayne 1-night trip
Posted 4 days ago
Sugarloaf Mountain Hotel

Find out more about Pleasant Ridge

Everything you need to know about Pleasant Ridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Ridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Ridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Ridge vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Ridge. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pleasant Ridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pleasant Ridge rentals

At Expedia, we put the best Pleasant Ridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasant Ridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Ridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Ridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Pleasant Ridge?

Yes, we have vacation rentals close to well known points of interest in Pleasant Ridge, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Pleasant Ridge has to offer?

On Mountain Home, Spectacular Mountain Views, Ski to the Door: This vacation home rental outside of Pleasant Ridge is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Pleasant Ridge?

Kennebec River and Wyman Lake are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Appalachian Trail and Embden Pond.

What are vacation rentals like in Pleasant Ridge?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Pleasant Ridge. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.