Holiday Homes in Chester

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Featured Holiday Homes in Chester

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is NZ$263
includes taxes & fees
1 Sept - 2 Sept
Whimsical Room & Private Bathroom in Historic Inn

WhiSki Cabin - 12 Acres With a Mountain View!

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
The price is NZ$1,646
includes taxes & fees
27 Aug - 28 Aug
WhiSki Cabin - 12 Acres With a Mountain View!

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (12)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is NZ$710
includes taxes & fees
17 Aug - 18 Aug
Charming Chester Farmhouse – peaceful and close to everything!

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (7)
"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "
The price is NZ$920
includes taxes & fees
18 Aug - 19 Aug
Cozy Home Near Downtown, Shops, and Restaurants.

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (3)
"What an amazing place! Very serene, clean and big enough for my family of 5. The hosts thought of everything to make our stay comfortable and memorable. Tough to beat the location! We will absolutely return!"
The price is NZ$723
includes taxes & fees
8 Sept - 9 Sept
Lake Front Family Friendly Escape

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is NZ$469
includes taxes & fees
6 Sept - 7 Sept
Family Friendly Hilltop House In Putney Vermont

Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

9.8 out of 10, Exceptional, (6)
"Very cozy and had all the essentials we needed for our trip! Check in and check out were easy, and it was perfect for our winter trip. It's a short drive to Okemo, which is super convenient - would definitely stay here again!"
The price is NZ$519
includes taxes & fees
7 Sept - 8 Sept
Charming Cavendish Guesthouse NEW SAUNA SEPT 2025!

The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
The price is NZ$558
includes taxes & fees
9 Sept - 10 Sept
The Carol - 10 minutes to Okemo & Newly Renovated- NEW SAUNA SEPT 2025!

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (1)
"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "
The price is NZ$318
includes taxes & fees
17 Aug - 18 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - Dog Friendly King Suite

10.0 out of 10, Exceptional, (1)
"We had an excellent stay, everything was so clean, the room was well appointed and there was even a little communal area with laundry, kitchen, snacks, and shuffleboard. We would absolutely recommend this motel, it’s a gem! "
The price is NZ$340
includes taxes & fees
17 Aug - 18 Aug
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock Mobility Impaired Accessible Suite

The price is NZ$257
includes taxes & fees
18 Aug - 19 Aug
Sleep Woodstock Mobility Impaired Accessible Suite

A charming 1820's farmhouse

10.0 out of 10, Exceptional, (27)
"this property had a very different feel because it was once an inn, which made it feel like we had the whole inn to ourselves, which was lovely. The place is spotless, everything you could possibly need is there, and it is beautifully decorated."
The price is NZ$2,218
includes taxes & fees
19 Aug - 20 Aug
A charming 1820's farmhouse

The Bridgewater House | Game Room | Hiking | Porch

9.6 out of 10, Exceptional, (7)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
The price is NZ$952
includes taxes & fees
19 Aug - 20 Aug
The Bridgewater House | Game Room | Hiking | Porch

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

The price is NZ$1,076
includes taxes & fees
17 Aug - 18 Aug
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

9.8 out of 10, Exceptional, (84)
"We had a great stay at this home for a long weekend skiing at Okemo. "
The price is NZ$726
includes taxes & fees
28 Aug - 29 Aug
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (101)
"This place was great! Convenient and clean. The beds were soooo comfy! We walked to town for groceries and dined out in town. We were there for a concert at Okemo which was just a few minutes away. We planned on hanging out back at the fire. Unfortunately, it rained so we hung out in the warm and inviting living room with a fire in the fireplace!! "
The price is NZ$677
includes taxes & fees
17 Aug - 18 Aug
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is NZ$654
includes taxes & fees
17 Aug - 18 Aug
Okemo's Back Room - in the heart of the village on the shuttle route!

Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath

10.0 out of 10, Exceptional, (1)
"We booked this for a last minute trip to Okemo and it was perfect for our group. It is only a couple minutes from Okemo base and a couple minutes from the cute downtown and a supermarket and craft beer store. The host was easy to talk to and extremely available, and very friendly and helpful! The house was in great condition, clean, and updated."
The price is NZ$1,796
includes taxes & fees
16 Aug - 17 Aug
Briggs Ski House | Group Ski Fun | 6 bdrm 4 bath

New Ludlow Village Home with Stunning Okemo Mountain View

10.0 out of 10, Exceptional, (6)
"Beautiful and clean place near Okemo with everything you need. "
The price is NZ$904
includes taxes & fees
16 Aug - 17 Aug
New Ludlow Village Home with Stunning Okemo Mountain View

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is NZ$871
includes taxes & fees
3 Sept - 4 Sept
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
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 Chester Hotel Reviews