Title: Chester Vacation Rentals from $289: Search Short-Term Rentals | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx89014)[Hotels in Chester](https://expedia.com/Chester-Hotels.d89014.Travel-Guide-Hotels)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d89014.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d89014.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chester vacation rentals

![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/d906295e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/0b80abe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/w1353h898x0y0-eb6e1bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/98b36931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Vermont Cabin · Mountain Views · Near Okemo

[](https://www.expedia.com/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information)

Chester

10/10

Exceptional

(4 reviews)

"Clean, spacous house, good location and great scenes of the mountains."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

pauline

$899 nightly

$1,007 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/4ae7b7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/35c5b21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/c539eb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/d409cd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chester Farmhouse Ski Retreat near Slopes

[](https://www.expedia.com/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information)

Chester Depot

9.6/10

Exceptional

(18 reviews)

"House was in a perfect location. The town was adorable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle A.

$378 nightly

$423 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/14ace880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/b15a729a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/70217bef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/0780f54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

[](https://www.expedia.com/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

Newfane

$528 nightly

$575 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/45000000/44400000/44397400/44397308/w1080h808x0y2-dd39b344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44400000/44397400/44397308/b5a6e268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/45000000/44400000/44397400/44397308/90-a120d7d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44400000/44397400/44397308/805d36b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

[](https://www.expedia.com/Ludlow-Hotels-Perfect-Okemo-Ski-Location-Winterplace-3-Bedroom-Condo-Short-Walk-To-Slopes.h44397308.Hotel-Information)

Okemo Village

10/10

Exceptional

(64 reviews)

"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nina

[](https://www.expedia.com/Ludlow-Hotels-Perfect-Okemo-Ski-Location-Winterplace-3-Bedroom-Condo-Short-Walk-To-Slopes.h44397308.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/c5d0a9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/b81f74eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/306e8880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Fully Renovated One-Room Schoolhouse on 22+ acres

[](https://www.expedia.com/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information)

Grafton

9.6/10

Exceptional

(168 reviews)

"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Philip

$318 nightly

$356 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/1f49fb0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/af3adada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/b112f7a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/f0bba734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Owl's Nest Treehouse

[](https://www.expedia.com/Alstead-Hotels-Owls-Nest-Treehouse.h111998634.Hotel-Information)

Alstead

10/10

Exceptional

(19 reviews)

"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Samantha R.

$309 nightly

$335 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Alstead-Hotels-Owls-Nest-Treehouse.h111998634.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/1a650c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/e3b7abc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/4c5c4ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/953a06fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

[](https://www.expedia.com/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

Walpole

10/10

Exceptional

(51 reviews)

"We had a very lovely stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

mary c.

$548 nightly

$595 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/4994716e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/c46d6757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/b907a89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snow and ski sports](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/1e2b3992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Long Trail House at Stratton Mountain Resort

[](https://www.expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

Stratton

8.6/10

Excellent

(83 reviews)

"Nice place and great location!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

$369 nightly

$417 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

[](https://www.expedia.com/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

Walpole

10/10

Exceptional

(8 reviews)

"Beautiful cozy cottage. Very clean. Wonderful host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gloria A.

$247 nightly

$268 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/w1179h778x0y0-d3dfa0ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/550afcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/7ae24bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/w1179h783x0y0-ad704094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

[](https://www.expedia.com/West-Dover-Hotels-Amazing-4-Bedroom-Location-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.Hotel-Information)

Dover

10/10

Exceptional

(13 reviews)

"great location easy access to the mountain and the pool was outstanding."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

jim f.

$1,031 nightly

$1,164 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Amazing-4-Bedroom-Location-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w505h683x260y0-72ec8d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/b42bfe82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w506h683x259y0-0378a284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w507h683x259y0-21bbc4b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

[](https://www.expedia.com/Newport-Hotels-Sugar-River-Treehouse.h99265952.Hotel-Information)

Newport

9.8/10

Exceptional

(21 reviews)

"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly R.

$346 nightly

$375 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Newport-Hotels-Sugar-River-Treehouse.h99265952.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96220000/96216500/96216492/5094120f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/97000000/96220000/96216500/96216492/5e473071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96216500/96216492/18ee80bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/97000000/96220000/96216500/96216492/835fddc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treehouse at Wise Pines- NoBo

[](https://www.expedia.com/Treehouse-At-Wise-Pines-NoBo.h96216492.Hotel-Information)

Woodstock

9.6/10

Exceptional

(15 reviews)

"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ethan

$172 nightly

$188 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Treehouse-At-Wise-Pines-NoBo.h96216492.Hotel-Information)

![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/fc371b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/7212c2d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/9b4bc035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/0d8dca3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

[](https://www.expedia.com/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.Hotel-Information)

Ludlow

$1,557 nightly

$1,712 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/11223970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/960544ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/c3fec788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/51cf9a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

[](https://www.expedia.com/Killington-Hotels-Ski-InSki-Out-Sunrise-Village-Condo-2BR.h120663196.Hotel-Information)

Killington

10/10

Exceptional

(36 reviews)

"Great ski-in, ski-out property."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristi C.

[](https://www.expedia.com/Killington-Hotels-Ski-InSki-Out-Sunrise-Village-Condo-2BR.h120663196.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559430/8e998a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559430/1c7cc9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559430/cdd156df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559430/639023fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trailside Village #3: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

[](https://www.expedia.com/Killington-Hotels-Trailside-Village-3-Slopeside-1BR-W-Hot-Tub-And-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559430.Hotel-Information)

Killington

9.6/10

Exceptional

(24 reviews)

"Loved it, great base of operations"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

josh B.

[](https://www.expedia.com/Killington-Hotels-Trailside-Village-3-Slopeside-1BR-W-Hot-Tub-And-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559430.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/12b9c5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/w1024h676x0y46-997613ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/w1024h676x0y46-4a569c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/0636cbc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

[](https://www.expedia.com/Cavendish-Hotels-Beautiful-Condominium-At-Castle-Hill-Resort.h67676844.Hotel-Information)

Cavendish

10/10

Exceptional

(23 reviews)

"Amazing place! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tara

$485 nightly

$543 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Cavendish-Hotels-Beautiful-Condominium-At-Castle-Hill-Resort.h67676844.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/05713f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/c3a6cd14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Bedrooms, Mountainside (Kettle Brook) | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/5237275c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Kettle Brook Two Bedroom 1 Bath Ski In/Out | Living room | 47-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/12d879f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Okemo Mountain Lodging by Vail Resorts

[](https://www.expedia.com/Ludlow-Hotels-Okemo-Mountain-Lodging.h32341945.Hotel-Information)

Clock Tower Base Area

7.8/10

Good

(28 reviews)

"I had an amazing time with my family, I will definitely be coming back "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Yenifer

$1,689 nightly

$1,908 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Okemo-Mountain-Lodging.h32341945.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/88000000/87820000/87816300/87816222/90138d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87820000/87816300/87816222/cf06e493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/88000000/87820000/87816300/87816222/c42e43ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/88000000/87820000/87816300/87816222/44fd3670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deerwood Hill \~ après ski cabin • hot tub • fire pit • Stratton • Manchester

[](https://www.expedia.com/South-Londonderry-Hotels-Stunning-Private-Cabin-Hot-Tub-Stratton-Bromley-Magic-Manchester.h87816222.Hotel-Information)

Londonderry

9.8/10

Exceptional

(23 reviews)

"Nice house, clean, easy access, well set up for family skiing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

L I.

$549 nightly

$620 total

Apr 15 - Apr 16

Total with taxes and fees

[](https://www.expedia.com/South-Londonderry-Hotels-Stunning-Private-Cabin-Hot-Tub-Stratton-Bromley-Magic-Manchester.h87816222.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/dc9c0b14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/8fc884c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/c08d6158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/dbd22110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Treehouse lifted up over a stocked trout pond up in the beautiful birch trees! 

[](https://www.expedia.com/Londonderry-Hotels-Treehouse-Lifted-Up-Over-A-Stocked-Trout-Pond-Up-In-The-Beautiful-Birch-Trees.h107553693.Hotel-Information)

Londonderry

8.2/10

Very Good

(11 reviews)

"We had a wonderful stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joshua

$502 nightly

$567 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Treehouse-Lifted-Up-Over-A-Stocked-Trout-Pond-Up-In-The-Beautiful-Birch-Trees.h107553693.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/4501ee4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/bdac3cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/w1170h1596x0y468-0a8fb230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/3902b9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table. 

[](https://www.expedia.com/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information)

Dover

9.8/10

Exceptional

(15 reviews)

"We enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveler

$505 nightly

$571 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08&regionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=APART_HOTEL)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=CHALET)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-06-21&d1=2026-06-21&endDate=2026-06-24&d2=2026-06-24&lodging=VILLA)

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## Top Chester Hotel Reviews

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg)

### Pointe at Castle Hill Resort

10/10 Excellent

"The staff is GREAT. No issues, just that the heated pool was still cold. "

[](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information)

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg)

### The Covered Bridge Inn

6/10 Okay

"Good job"

[](https://expedia.com/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information)

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg)

### On The River Inn

10/10 Excellent

"the lady at the check in and the waiter were amazing"

[](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg)

### Best Western Plus Keene Hotel

4/10 Poor

"Sink didn't drain properly, smoke detector was gone only two wires, bathroom door delaminated. Outside door card entry broken."

[](https://expedia.com/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information)

![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg)

### Hampton Inn and Suites Manchester

10/10 Excellent

"Clean, updated rooms. Great breakfast for continental."

[](https://expedia.com/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg)

### Colonial Motel And Spa

2/10 Terrible

"What a dump"

[](https://expedia.com/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information)

![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg)

### Hideaway Inn Mt. Snow

6/10 Okay

"The bath soap container was empty. I asked a hotel staff member if she could refill the dispenser and she said she would bring it to my room in a few minutes. She never showed up as promised. I passed her on the way out 45 minutes later. She look at me and went on her business. "

[](https://expedia.com/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information)

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg)

### Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"It was great to have so many amenities on site. It felt like a home away from home. "

[](https://expedia.com/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information)

![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/4412313e_y.jpg)

### The Palmer House Resort, an Ascend Collection Hotel

4/10 Poor

"Room was dusty ans did not appear to have been cleaned properly, had an allergy flair up. Found hairs in the bathroom. No other rooms available had to leave. Had to leave to another place. However staff was understanding, polite and tried to accommodate. It just didn’t work for us. "

[](https://expedia.com/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information)

## Find out more about Chester

**Everything you need to know about Chester vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Chester vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $289 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Chester rentals**

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Chester ](https://expedia.com/Chester-Private-Vacation-Homes.d89014-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Chester ](https://expedia.com/Chester-Condos.d89014-aaCondos.Travel-Guide-Accommodation)
- [Apartments in Chester ](https://expedia.com/Chester-Apartments.d89014-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Chester ](https://expedia.com/Chester-Cottages.d89014-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Chester ](https://expedia.com/Chester-Cabins.d89014-aaCabins.Travel-Guide-Accommodation)
- [Chalets in Chester ](https://expedia.com/Chester-Chalets.d89014-aaChalets.Travel-Guide-Accommodation)
- [B&B in Chester ](https://expedia.com/Chester-Bed-And-Breakfast.d89014-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Chester ](https://expedia.com/Chester-Resorts.d89014-aaResorts.Travel-Guide-Accommodation)
- [Farmstay in Chester ](https://expedia.com/Chester-Agritourism.d89014-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Chester ](https://expedia.com/Chester-Motels.d89014-aaMotels.Travel-Guide-Accommodation)
- [Aparthotels in Chester ](https://expedia.com/Chester-Apart-Hotels.d89014-aaApartHotels.Travel-Guide-Accommodation)
- [Villas in Chester ](https://expedia.com/Chester-Villas.d89014-aaVillas.Travel-Guide-Accommodation)
- [Guest Houses in Chester ](https://expedia.com/Chester-Guest-Houses.d89014-aaGuestHouses.Travel-Guide-Accommodation)
- [Lodges in Chester ](https://expedia.com/Chester-Lodges.d89014-aaLodges.Travel-Guide-Accommodation)
- [Inns in Chester ](https://expedia.com/Chester-Inns.d89014-aaInns.Travel-Guide-Accommodation)
- [RV Parks in Chester ](https://expedia.com/Chester-RV-Parks.d89014-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Chester?

### What are some of the best vacation rentals in Chester?

### How many vacation rentals will I find in Chester?

### What’s there to see and do in Chester?

### What’s a vacation rental in Chester like?

### Expedia's Latest Trends

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- [Hotels in St. Albans](https://expedia.com/St-Albans-Hotels.d6057383.Travel-Guide-Hotels)
- [Hotels in Newport](https://expedia.com/Newport-Hotels.d7047.Travel-Guide-Hotels)
- [Hotels in Montpelier](https://expedia.com/Montpelier-Hotels.d8798.Travel-Guide-Hotels)
- [Hotels in Colchester](https://expedia.com/Colchester-Hotels.d91135.Travel-Guide-Hotels)
- [Hotels in Woodstock](https://expedia.com/Woodstock-Hotels.d10868.Travel-Guide-Hotels)
- [Hotels in Springfield](https://expedia.com/Springfield-Hotels.d10292.Travel-Guide-Hotels)
- [Hotels in Manchester](https://expedia.com/Manchester-Hotels.d129374.Travel-Guide-Hotels)
- [Hotels in Williston](https://expedia.com/Williston-Hotels.d10411.Travel-Guide-Hotels)
- [Hotels in Killington](https://expedia.com/Killington-Hotels.d10780.Travel-Guide-Hotels)
- [Hotels in Burlington](https://expedia.com/Burlington-Hotels.d601763.Travel-Guide-Hotels)
- [Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d8852.Travel-Guide-Hotels)
- [Hotels in Ludlow](https://expedia.com/Ludlow-Hotels.d8496.Travel-Guide-Hotels)
- [Hotels in Warren](https://expedia.com/Warren-Hotels.d171287.Travel-Guide-Hotels)

Flights

- [Flights to Stowe](https://expedia.com/Cheap-Flights-To-Stowe.d6057386.Travel-Guide-Flights)
- [Flights to Burlington](https://expedia.com/Cheap-Flights-To-Burlington.d601763.Travel-Guide-Flights)

Cars

- [Car rentals in Burlington](https://expedia.com/Car-Rentals-In-Burlington.d601763.Car-Rental-Guide)

Activities

- [Things to do in Montpelier](https://expedia.com/Things-To-Do-In-Montpelier.d8798.Travel-Guide-Activities)

Vacation Rentals

- [Killington Rentals](https://expedia.com/Killington-Vacation-Rentals.d10780.Travel-Guide-VacationRentals)

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