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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/8f3740a5.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)

![Exterior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/0b80abe1.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)

![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/d409cd42.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/df792487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Chester Farmhouse near Near VT 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.

$380 nightly

$426 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/f0bba734.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)

![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111998700/111998634/ab414fef.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

(20 reviews)

"Amazing place, cozy, clean and organized. I loved it and I want to come back again."

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

Alex F.

$309 nightly

$335 total

Mar 29 - Mar 30

Total with taxes and fees

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

![Restaurant](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/a16eeef9.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

$366 nightly

$413 total

Apr 15 - Apr 16

Total with taxes and fees

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

![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)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/becbfa0d.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)

### 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 30 - Mar 31

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/100000000/99270000/99266000/99265952/w505h683x260y0-72ec8d92.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)

![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)

### 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 treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. "

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

Ashley P.

$343 nightly

$372 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Newport-Hotels-Sugar-River-Treehouse.h99265952.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/121000000/120620000/120618700/120618609/2220bc31.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)

![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)

### 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 28 - Mar 29

Total with taxes and fees

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

![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)

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

### Treehouse at Wise Pines- NoBo

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

![Fitness facility](https://images.trvl-media.com/lodging/68000000/67680000/67676900/67676844/0636cbc6.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)

![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)

### 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

$483 nightly

$541 total

Mar 27 - Mar 28

Total with taxes and fees

[](https://www.expedia.com/Cavendish-Hotels-Beautiful-Condominium-At-Castle-Hill-Resort.h67676844.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](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/953a06fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/18ad0df8.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)

### 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)

![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)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.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.

$234 nightly

$254 total

Mar 29 - Mar 30

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/23000000/22870000/22865900/22865847/fe1abb51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/344617b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ad47e382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/faf90773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information)

Ludlow

9.8/10

Exceptional

(108 reviews)

"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."

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

Hannah M.

$424 nightly

$461 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/a93fa1dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/1aff520b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/a4957511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/23000000/22770000/22769000/22768970/67c634a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

[](https://www.expedia.com/Ludlow-Hotels-Beautifully-Updated-Unique-Village-Home.h22768970.Hotel-Information)

Ludlow

9.8/10

Exceptional

(85 reviews)

"We had a great stay at this home for a long weekend skiing at Okemo. "

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

Lisa W.

$424 nightly

$461 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Beautifully-Updated-Unique-Village-Home.h22768970.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/1b33e3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/2382fc0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/e1e135fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/104000000/103590000/103582500/103582490/w1179h1473x0y0-1190758b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Romantic Riverbed Treehouse - hot tub & new sauna!

[](https://www.expedia.com/Londonderry-Hotels-Romantic-Riverbed-Treehouse-Hot-Tub-New-Sauna.h103582490.Hotel-Information)

londonderry

9.6/10

Exceptional

(5 reviews)

"Great little space"

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

John

$567 nightly

$641 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Romantic-Riverbed-Treehouse-Hot-Tub-New-Sauna.h103582490.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/6cd80eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/0a827c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/w956h736x34y34-3e10a6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/de082b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wellness Getaway with a Personal Sauna, and Private River Beach!

[](https://www.expedia.com/Newfane-Hotels-Wellness-Getaway-With-A-Personal-Sauna.h106418444.Hotel-Information)

Newfane

10/10

Exceptional

(3 reviews)

"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "

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

Joseph P.

$229 nightly

$256 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Newfane-Hotels-Wellness-Getaway-With-A-Personal-Sauna.h106418444.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/81ff9d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/0592805f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/6b0e5b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/83d1a856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Front Family Friendly Escape

[](https://www.expedia.com/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information)

Newport

10/10

Exceptional

(4 reviews)

"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"

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

Ann R.

$318 nightly

$345 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/3081d55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/179138f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/00165d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103490000/103490000/103489995/ff9732b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Insanely romantic treehouse perched next to a stream and rolling hills.

[](https://www.expedia.com/Londonderry-Hotels-Insanely-Romantic-Treehouse-Perched-Next-To-A-Stream-And-Rolling-Hills.h103489995.Hotel-Information)

Londonderry

10/10

Exceptional

(2 reviews)

"Very nice secluded treehouse. We would definitely recommend!"

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

Beth H.

$776 nightly

$877 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Insanely-Romantic-Treehouse-Perched-Next-To-A-Stream-And-Rolling-Hills.h103489995.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/6a529202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/4ab54715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/a073bac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111559500/111559434/a9b4d8fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trailside Six: Ski-On/Off Condo for 8 with Private Hot Tub & Sauna. Ski Deals Too.

[](https://www.expedia.com/Killington-Hotels-Trailside-Village-6-Slopeside-3BR2BA-Hot-Tub-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559434.Hotel-Information)

Killington

9.6/10

Exceptional

(72 reviews)

"Amazing ski-in/out property slope-side! We enjoyed our stay very much! "

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

Jason

[](https://www.expedia.com/Killington-Hotels-Trailside-Village-6-Slopeside-3BR2BA-Hot-Tub-Sauna-Ski-InOut-With-Discounted-Lift-Tickets.h111559434.Hotel-Information)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/0d7d95c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/60d61b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/3029491b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/f211031c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

[](https://www.expedia.com/Mount-Holly-Hotels-Charming-Family-Ski-Chalet-Less-Than-5-Minutes-Drive-To-OkemoJackson-Gore.h41897267.Hotel-Information)

Mt Holly

9.8/10

Exceptional

(41 reviews)

"Wonderful cabin, well stocked, host was attentive and quick to address any questions."

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

Eyal O.

$482 nightly

$540 total

Apr 26 - Apr 27

Total with taxes and fees

[](https://www.expedia.com/Mount-Holly-Hotels-Charming-Family-Ski-Chalet-Less-Than-5-Minutes-Drive-To-OkemoJackson-Gore.h41897267.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/109000000/108440000/108431000/108430968/5cd35f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108440000/108431000/108430968/ff9073c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108440000/108431000/108430968/08bac740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/109000000/108440000/108431000/108430968/2b070491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

[](https://www.expedia.com/Ludlow-Hotels-Cozy-Slopeside-Escape-Ski-InOut-Condo-At-Okemo.h108430968.Hotel-Information)

Okemo Village

10/10

Exceptional

(12 reviews)

"We had a great time , the location was amazing and the owner responded very quickly for any questions or concerns "

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

Thomas B.

$464 nightly

$524 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Cozy-Slopeside-Escape-Ski-InOut-Condo-At-Okemo.h108430968.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=2026-04-09&endDate=2026-04-10&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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=VACATION_HOME)

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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=CONDO)

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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=COTTAGE)

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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=APART_HOTEL)

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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=APARTMENT)

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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=VILLA)

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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=CHALET)

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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

"There's a cute little town nearby with a great coffee shop. "

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

" Very cozy. Lovely breakfast. Fun smores"

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

![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1_y.jpg)

### Stone Hearth Inn and Eatery

10/10 Excellent

"Beautiful place. Rustic and restored beautifully to keep the charm. Talked with the owner over breakfast. Family business with an amazing restaurant. We will stay there again! "

[](https://expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.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

8/10 Good

"Room was fine. Only stayed one night for a quick trip. Didn't realize that the restaurant was closed on Sundays. Was looking for a meal after a long drive, but there were plenty of places to eat in the area. "

[](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

"Every employee was incredibly friendly, even if only passing us in the foyer or hallways. Stacy, the operations manager, was especially engaging, knowledgeable and helpful as we were deciding what to do for dinner and what events and venues were worth visiting. We took all of her suggestions and were thrilled when she was spot-on across the board, from Ye Olde Tavern to the syrup-making tour at Dutton’s to the Vermont Country Store. She’s an asset to your operations."

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

![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)

## 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?

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- [Hotels in Essex Junction](https://expedia.com/Essex-Junction-Hotels.d7853.Travel-Guide-Hotels)
- [Hotels in White River Junction](https://expedia.com/White-River-Junction-Hotels.d6294.Travel-Guide-Hotels)
- [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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