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Top Holiday Rentals in Chester

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 £755
includes taxes & fees
16 Jul - 17 Jul
WhiSki Cabin - 12 Acres With a Mountain View!

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 £164
includes taxes & fees
20 Jul - 21 Jul
Whimsical Room & Private Bathroom in Historic Inn

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (11)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is £323
includes taxes & fees
30 Jul - 31 Jul
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, (5)
"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 £381
includes taxes & fees
16 Jul - 17 Jul
Cozy Home Near Downtown, Shops, and Restaurants.

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (2)
"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 £395
includes taxes & fees
22 Jul - 23 Jul
Lake Front Family Friendly Escape

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

The price is £162
includes taxes & fees
22 Jul - 23 Jul
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

Cozy Cavendish Bunk minutes to Okemo

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 £181
includes taxes & fees
16 Jul - 17 Jul
Cozy Cavendish Bunk minutes to Okemo

Sleep Woodstock - Dog Friendly King Suite

The price is £122
includes taxes & fees
21 Jul - 22 Jul
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock Mobility Impaired Accessible Suite

The price is £108
includes taxes & fees
21 Jul - 22 Jul
Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is £109
includes taxes & fees
22 Jul - 23 Jul
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - Deluxe Suite

2.0 star property
The price is £277
includes taxes & fees
17 Jul - 18 Jul
Sleep Woodstock - Deluxe 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 £1,005
includes taxes & fees
1 Aug - 2 Aug
A charming 1820's farmhouse

The Bridgewater House | Game Room | Hiking | Golf

9.4 out of 10, Exceptional, (6)
"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 £417
includes taxes & fees
23 Jul - 24 Jul
The Bridgewater House | Game Room | Hiking | Golf

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 £323
includes taxes & fees
17 Jul - 18 Jul
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, (100)
"Great location and house was very nice."
The price is £312
includes taxes & fees
17 Jul - 18 Jul
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 £254
includes taxes & fees
21 Jul - 22 Jul
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 £825
includes taxes & fees
16 Jul - 17 Jul
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 £541
includes taxes & fees
16 Jul - 17 Jul
New Ludlow Village Home with Stunning Okemo Mountain View

NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House

The price is £668
includes taxes & fees
16 Jul - 17 Jul
NEW Hot Tub/Lakeview/Pool Table/Okemo Ski House

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (5)
"We enjoyed the quiet and convenience of this location to Mt. Snow. It was clean and well stocked. Host was kind and responsive."
The price is £582
includes taxes & fees
16 Jul - 17 Jul
The dreamiest place in Southern Vermont!
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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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?

Quaint lakefront home with a private deck, firepit, and dock: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Chester?

Choose from 32 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. Vermont Country Store and Plummer's Sugar House are a couple of places you'll find in the wider area.

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.