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Pleasant Ridge Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

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.
The price is ￥15,513
￥25,364 total
includes taxes & fees
Dec 7 - Dec 8
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.
The price is ￥118,674
￥200,880 total
includes taxes & fees
Dec 7 - Dec 8
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.
The price is ￥100,524
￥163,850 total
includes taxes & fees
Dec 7 - Dec 8
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.
The price is ￥54,856
￥126,162 total
includes taxes & fees
Dec 7 - Dec 8
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

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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.