Town of Jackson Holiday Rentals

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Top Holiday Rentals Destinations in Town of Jackson

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (200)
"Another wonderful long weekend at this cozy, comfortable oasis. Simply bliss. See you next year!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Walking Distance to Everything! Pet Friendly with Fully Fenced Yard! Track/SPAC

10.0 out of 10, Exceptional, (13)
"Enjoyed our stay. Great location and really nice house and fenced in yard. Walking distance to town. "
Walking Distance to Everything! Pet Friendly with Fully Fenced Yard! Track/SPAC

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AU$639
includes taxes & fees
3 Dec - 4 Dec
Long Trail House at Stratton Mountain Resort

Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (211)
"Place was amazing very secluded but close enough to get into town and do things. Our longest drive to go do something was only nine minutes away. Everything was as promised. The only issue we had was the back door entry. The hot tub is right there and when we were standing outside watching nature, we saw bees and wasps going underneath the hot tub. so because we were both chickens, we never went into the hot tub. I probably should’ve called the owner to let him know, but I was a little...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (54)
"We rented the barn as an overflow space from the main house. The barn has everything you need and is a really cool spot to sit and view the entire property."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

NEW 5 BR 4 Bath IMPECCABLE home Community Indoor pool! EV charger! Wkly discount

10.0 out of 10, Exceptional, (26)
"Barbara was so easy and nice to communicate with! The house was as described/looks in pictures and had everything we needed for our family (13 people), including a basement area where the kids could hang out and watch tv while we cooked in the beautiful kitchen! Great area with a clubhouse down the road for use. Would definitely stay again! "
NEW 5 BR 4 Bath IMPECCABLE home Community Indoor pool! EV charger! Wkly discount

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.6 out of 10, Excellent, (20)
"Wonderful stay. Thanks again"
The price is AU$498
includes taxes & fees
10 Dec - 11 Dec
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

Private and Artistic cabin, Pet friendly, no cleaning fee

10.0 out of 10, Exceptional, (255)
"We enjoyed staying at Rik’s cabin. It’s a unique space and a wonderful experience. His bread is delicious and the fireplace was delightful after a day out. Rik is a gracious host. Highly recommended if you want something different. "
Private and Artistic cabin, Pet friendly, no cleaning fee

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (196)
"Beautiful time of the year to enjoy this property and the surrounding woods and trails, plus Manchester. Our dogs love it here. "
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (41)
"Can't beat the location. We had a great stay."
The price is AU$416
includes taxes & fees
3 Dec - 4 Dec
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub

9 Bedrooms🏡Heated Pool🏊HotTub🛁By Ski West Mtn⛷️Town🌆SPAC🎵Lake🏖️Casino🎰Golf⛳️ Track🏇

10.0 out of 10, Exceptional, (17)
"Rowing team from Duxbury MA, participating in Head of the Fish Regatta"
9 Bedrooms🏡Heated Pool🏊HotTub🛁By Ski West Mtn⛷️Town🌆SPAC🎵Lake🏖️Casino🎰Golf⛳️ Track🏇

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

9.6 out of 10, Exceptional, (45)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

XL Cozy Home Nr Ski Mtn+Lk George w/Indoor HotTub

9.4 out of 10, Exceptional, (3)
"My family of 5 stayed 4 nights here after a whirlwind stay in NYC. It was just the ticket to get away from the craziness, recover and enjoy nature a bit. Overall our stay was nice, but I wouldn't rate it 5 stars. There were a few things that could’ve made it a bit nicer. The yard needed mowing pretty badly, the beds were creaky and a bit hard, and little things (like the washing machine gasket was moldy and the air hockey table not quite working) showed that a little more TLC would make this an...
XL Cozy Home Nr Ski Mtn+Lk George w/Indoor HotTub

Welcome to Beautiful Saratoga Springs Location

9.4 out of 10, Exceptional, (37)
"We thoroughly enjoyed our stay and everything about the place from its location to all the amenities. We would definitely stay here again. "
The price is AU$683
includes taxes & fees
3 Dec - 4 Dec
Welcome to Beautiful Saratoga Springs Location

Walkout basement with bar and hot tub!

9.4 out of 10, Exceptional, (10)
"The place was great and exactly as described! Steven was very kind and helpful with any questions and responded immediately everytime. Will definitely be coming back! Thanks Steven! "
The price is AU$347
includes taxes & fees
3 Dec - 4 Dec
Walkout basement with bar and hot tub!

Great Place to get away and have clean fresh air surround you!

9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
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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Beautiful view of the beach with palm trees

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