Title: Chester Vacation Rentals from CA $429: Short-Term Rentals for 2026 | Expedia.ca

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-06-26&endDate=2026-06-28&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/w1353h898x0y0-eb6e1bb7.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)

![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.ca/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information)

Chester

10/10

Exceptional

(3 reviews)

"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. "

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

Donald M.

CA $858

CA $1,534 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/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)

![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/95264663.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)

![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)

### Chester Farmhouse Ski Retreat near Slopes

[](https://www.expedia.ca/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.

CA $307

CA $608 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/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)

![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)

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

### Owl's Nest Treehouse

[](https://www.expedia.ca/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.

CA $375

CA $466 total

includes taxes & fees

Mar 3 - Mar 4

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

![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)

![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)

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

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

Grafton

9.6/10

Exceptional

(167 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

CA $232

CA $504 total

includes taxes & fees

Mar 3 - Mar 4

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

![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)

![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.ca/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

Walpole

10/10

Exceptional

(50 reviews)

"We had a very lovely stay. "

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

mary c.

CA $378

CA $799 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/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)

![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)

![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)

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

[](https://www.expedia.ca/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.

CA $279

CA $346 total

includes taxes & fees

Mar 3 - Mar 4

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

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/de082b20.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)

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

[](https://www.expedia.ca/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.

CA $184

CA $348 total

includes taxes & fees

Mar 18 - Mar 19

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/88000000/87820000/87816300/87816222/43852f45.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)

![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.ca/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.

CA $284

CA $804 total

includes taxes & fees

Mar 3 - Mar 4

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

![Property grounds](https://images.trvl-media.com/lodging/100000000/99270000/99266000/99265952/w509h683x258y0-02581c4d.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.ca/Newport-Hotels-Sugar-River-Treehouse-Relaxing-Escape-Among-The-Trees-On-The-Serene-Sugar-River.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.

CA $246

CA $517 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Newport-Hotels-Sugar-River-Treehouse-Relaxing-Escape-Among-The-Trees-On-The-Serene-Sugar-River.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)

![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96216500/96216492/18ee80bb.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)

![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.ca/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

CA $205

CA $254 total

includes taxes & fees

Mar 16 - Mar 17

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

![Interior](https://images.trvl-media.com/lodging/108000000/107560000/107553700/107553693/20d51d16.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.ca/Londonderry-Hotels-Treehouse-Lifted-Up-Over-A-Stocked-Trout-Pond-Up-In-The-Beautiful-Birch-Trees.h107553693.Hotel-Information)

Londonderry

8.8/10

Excellent

(10 reviews)

"We had a wonderful stay."

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

Joshua

CA $448

CA $765 total

includes taxes & fees

Mar 3 - Mar 4

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

![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)

![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)

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

[](https://www.expedia.ca/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.

CA $540

CA $1,218 total

includes taxes & fees

Mar 3 - Mar 4

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

![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)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/109000000/108440000/108431000/108430968/e94c67f7.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)

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

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

Okemo Village

10/10

Exceptional

(11 reviews)

"Location was perfect for skiing. Hosts were responsive and the stay was pleasant. Would book again."

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

Paul T.

CA $408

CA $868 total

includes taxes & fees

Apr 1 - Apr 2

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

![Interior](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/b907a89a.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)

![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)

### Long Trail House at Stratton Mountain Resort

[](https://www.expedia.ca/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

CA $486

CA $605 total

includes taxes & fees

Apr 2 - Apr 3

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

![Interior](https://images.trvl-media.com/lodging/121000000/120670000/120663200/120663196/c3fec788.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)

![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.ca/Killington-Hotels-Ski-InSki-Out-Sunrise-Village-Condo-2BR.h120663196.Hotel-Information)

Killington

10/10

Exceptional

(35 reviews)

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

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

Kristi C.

CA $693

CA $1,283 total

includes taxes & fees

Mar 3 - Mar 4

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

![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/w1170h748x0y892-f0ce30fb.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)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/bdac3cda.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.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information)

Dover

10/10

Exceptional

(11 reviews)

"We enjoyed our stay."

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

Anonymous traveller

CA $306

CA $788 total

includes taxes & fees

Mar 4 - Mar 5

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

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/c07b5f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/32d5ed92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/4623c2dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/10b7883b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

[](https://www.expedia.ca/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information)

Cavendish

10/10

Exceptional

(14 reviews)

"This was absolutely perfect. Every part of the cabin was well thought out from design to decor. We had such an amazing time and already want to plan another getaway to this place. "

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

Adam B.

CA $293

CA $495 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/73e1d55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w960h638x0y1-6a5c7328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Family Friendly Hilltop House In Putney Vermont

[](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

Putney

9.4/10

Exceptional

(59 reviews)

"The host and her daughter were lovely and kind and very quick with all communication."

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

Susan O.

CA $214

CA $402 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/245ee0c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/2f6c29d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/db97c90e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89070000/89068200/89068117/a7539bc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

[](https://www.expedia.ca/Londonderry-Hotels-Summit-View-Cottage-Close-To-Stratton-Mountain.h89068117.Hotel-Information)

Londonderry

10/10

Exceptional

(10 reviews)

"Great location, well-designed house, and a beautiful view."

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

Marcel P.

CA $522

CA $1,114 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Londonderry-Hotels-Summit-View-Cottage-Close-To-Stratton-Mountain.h89068117.Hotel-Information)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/90000000/89990000/89988000/89987989/3ba6c1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/90000000/89990000/89988000/89987989/0e5ae0d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/90000000/89990000/89988000/89987989/e29b1e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89990000/89988000/89987989/ae0edcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.

[](https://www.expedia.ca/Bondville-Hotels-7-Guest-Renovated-Stratton-Condo-With-Fireplace-4-Minutes-To-Stratton-Village.h89987989.Hotel-Information)

Winhall

10/10

Exceptional

(22 reviews)

"Beautiful location close to ski resorts and towns. Well maintained property with all the amenities of home. Had a wonderful time staying here! "

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

Caroline F.

CA $203

CA $497 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Bondville-Hotels-7-Guest-Renovated-Stratton-Condo-With-Fireplace-4-Minutes-To-Stratton-Village.h89987989.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.ca/Hotel-Search?startDate=2026-03-16&endDate=2026-03-17&regionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_89014)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CONDO)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CHALET)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America&regionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA)

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## Top Chester Hotel Reviews

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg)

### Pointe at Castle Hill Resort

10/10 Excellent

"Clean room, friendly staff, great pool and hot tub, and very conveniently located close to Okemo. "

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

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Very clean and comfortable "

[](https://expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information)

![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg)

### Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Good location for our needs and very comfortable"

[](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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

"Great"

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

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg)

### Hampton Inn Brattleboro

10/10 Excellent

"Staff and clean room"

[](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information)

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg)

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

10/10 Excellent

"clean and spacious room "

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

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg)

### Colonial Motel And Spa

10/10 Excellent

"Room. Staff"

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

![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg)

### Woodstock Inn & Resort

10/10 Excellent

"Very clean, high end, friendly staff "

[](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information)

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg)

### The Manchester View

10/10 Excellent

"The room was very nice and confortable."

[](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

## Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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

## Frequently asked questions

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

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