Chester Holiday Rentals

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Holiday Rentals in Chester

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.2 out of 10, Wonderful, (15)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (148)
"The area was amazing and the views were incredible. "
The price is AU$574
includes taxes & fees
11 Dec - 12 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

9.6 out of 10, Exceptional, (54)
"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is AU$698
includes taxes & fees
3 Dec - 4 Dec
Long Trail House at Stratton Mountain Resort

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

9.0 out of 10, Wonderful, (42)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

VT Cabin overlooking the West River and Village

10.0 out of 10, Exceptional, (27)
"We loved our stay! Such lovely cabin! We loved it so much that we were bummed we didn’t book a longer stay. It had everything we needed to make our stay comfortable."
The price is AU$509
includes taxes & fees
1 Dec - 2 Dec
VT Cabin overlooking the West River and Village

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}

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

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (19)
"Beautiful property and wonderful host. Very welcoming and cozy, and within a quick drive of lots of great activities. I would definitely stay here again!"
The price is AU$278
includes taxes & fees
1 Dec - 2 Dec
Treehouse at Wise Pines- SoBo

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (29)
"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...
Walk to Mount Snow, Cozy, Clean and Comfortable!

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (30)
"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.0 out of 10, Wonderful, (26)
"The tiny houses were cute and well equipped. They were ideal for 2 friends traveling together having their own space. I would definitely rent this property again. Only negative was having 3 empty propane tanks when we wanted to use the fire table(something to be added to the maintenance checklust) however once i text them they dropped a fresh tank off that same evening."
The price is AU$690
includes taxes & fees
2 Dec - 3 Dec
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (33)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
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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Other types of properties in Chester you may be interested in

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (73)
"My husband and I stayed here for a night. Communication was great. Beautiful old inn. The best part was the owners daughter/husband are chefs! Like...gourmet chefs! I think I had the best breakfast I've ever had in my life here. Just a lovely family owned - beautiful VT Inn. Would stay again in a heartbeat!"
The price is AU$375
includes taxes & fees
5 Dec - 6 Dec
Stone Hearth Inn and Eatery

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (483)
"The overall experience was great. "
The price is AU$590
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort

Hampton Inn and Suites Manchester

2.5 star property
9.6 out of 10, Exceptional, (1094)
"Like cleanliness and the bed and pillows were good."
The price is AU$230
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn and Suites Manchester
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to DaVallia Art & Accents, or you can select a more secluded option if you're looking for a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffee shops and restaurants.

What are some of the best holiday rentals that Chester has to offer?

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree!: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chester?

Choose from 37 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of the family-friendly sights. While in the area, you can also visit popular places such as Okemo Mountain Resort and Stratton Mountain Resort.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals feature extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.