Title: Chester Vacation Home Rentals from CA $424: Search Top Private Vacation Homes for Rent | Expedia.ca

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## Check prices for these dates

Next weekend

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-13&endDate=2026-03-15&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 homes

![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/102000000/101480000/101473400/101473310/95264663.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

(17 reviews)

"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "

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

Lori N.

CA $221

CA $499 total

includes taxes & fees

Jan 19 - Jan 20

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

![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)

![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)

![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 $874

CA $1,562 total

includes taxes & fees

Jan 28 - Jan 29

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

![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

(19 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 $250

CA $514 total

includes taxes & fees

Jan 28 - Jan 29

[](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/20000000/19890000/19887200/19887179/a4ec6964.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)

![Interior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/73e1d55a.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 property was beautiful--great views, super peaceful, and fabulous hosts. "

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

Louis T.

CA $229

CA $424 total

includes taxes & fees

Jan 28 - Jan 29

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

![Exterior](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/6b0e5b60.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)

![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.ca/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.

CA $150

CA $475 total

includes taxes & fees

Jan 27 - Jan 28

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

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/3e9df2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/29b5b165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/0444e51c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/4c677d14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

[](https://www.expedia.ca/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information)

Londonderry

8.0/10

Very good

(1 review)

"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "

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

Christine M.

CA $352

CA $692 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.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)

![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/953a06fc.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.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 $401

CA $826 total

includes taxes & fees

Jan 21 - Jan 22

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/8d9f525d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/e0a6d5c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/6cc8f8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/4e846ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

[](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information)

Keene

10/10

Exceptional

(2 reviews)

"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...

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

Xilin J.

CA $293

CA $830 total

includes taxes & fees

Jan 26 - Jan 27

[](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/668fb777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/88c2ea85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/1d81a334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123950000/123942400/123942314/7384c305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Secluded Vermont Chalet w/ Sweeping Mountain Views

[](https://www.expedia.ca/East-Dover-Hotels-Secluded-Vermont-Chalet-W-Sweeping-Mountain-Views.h123942314.Hotel-Information)

Dover

CA $194

CA $717 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/East-Dover-Hotels-Secluded-Vermont-Chalet-W-Sweeping-Mountain-Views.h123942314.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)

![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)

![Indoor pool](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/9dbc4479.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.ca/West-Dover-Hotels-Amazing-4-Bedroom-Location-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.Hotel-Information)

Dover

10/10

Exceptional

(10 reviews)

"Nice in all respects,"

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

Ken

CA $994

CA $2,017 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/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/125000000/124540000/124538100/124538047/w1198h799x2y0-00d2a21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/w2996h1998x4y0-035fc1b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/2a7ccda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels](https://images.trvl-media.com/lodging/125000000/124540000/124538100/124538047/68e0da24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Woods · Secluded Vermont Cabin Retreat

[](https://www.expedia.ca/West-Wardsboro-Hotels-Stratton-Woods-Secluded-Vermont-Cabin-Retreat.h124538047.Hotel-Information)

Wardsboro

CA $237

CA $343 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/West-Wardsboro-Hotels-Stratton-Woods-Secluded-Vermont-Cabin-Retreat.h124538047.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)

![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.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information)

Dover

9.8/10

Exceptional

(6 reviews)

"We enjoyed our stay."

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

Anonymous traveller

CA $374

CA $874 total

includes taxes & fees

Jan 26 - Jan 27

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

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/244b8f71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/809fbf0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/e40e49c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0b045033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information)

Bridgewater

9.6/10

Exceptional

(17 reviews)

"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "

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

Gerri B.

CA $354

CA $894 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.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)

![Exterior](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/ad47e382.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)

![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22870000/22865900/22865847/1516e7fd.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.ca/Ludlow-Hotels-Short-Walk-To-Shops.h22865847.Hotel-Information)

Ludlow

9.8/10

Exceptional

(104 reviews)

"Had a wonderful stay. Clean,well kept and cozy."

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

Edwin G.

CA $319

CA $632 total

includes taxes & fees

Jan 20 - Jan 21

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

![Interior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/620d544b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/a4954c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![A heated pool](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/cea2d009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/d295676b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information)

Stratton

7.8/10

Good

(52 reviews)

"Location was great, pool, hot tubs and sauna were great"

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

Lin M.

CA $212

CA $562 total

includes taxes & fees

Jan 22 - Jan 23

[](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/f89f88e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/96f31790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/c1c7a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/100000000/99995200/99995104/5ada38fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Dorset Cottage Retreat. 

[](https://www.expedia.ca/Dorset-Hotels-Charming-Dorset-Cottage-Retreat.h99995104.Hotel-Information)

Dorset

10/10

Exceptional

(7 reviews)

"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."

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

Sarah S.

CA $412

CA $1,017 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Dorset-Hotels-Charming-Dorset-Cottage-Retreat.h99995104.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/59f7968b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/f45bf329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/1562dce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/e9ad80e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

[](https://www.expedia.ca/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information)

Jamaica

9.6/10

Exceptional

(23 reviews)

"Absolutely a wonderful place to vacation. The house is comfortable and warming. The hosts went above and beyond to make our stay great and responded to our questions promptly. We will definitely rent again. "

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

Lee Anna C.

CA $515

CA $1,390 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/c3df7e46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/22345953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/1b212a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90700000/90693000/90692944/9f5da7f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Large Killington Area Home | Sleeps 7 | Game Room

[](https://www.expedia.ca/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.Hotel-Information)

Bridgewater

9.6/10

Exceptional

(7 reviews)

"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."

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

Owen C.

CA $550

CA $1,107 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Bridgewater-Hotels-Bridgewater-Inn-2-King-Beds-Game-Room-Skiing.h90692944.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)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/42000000/41900000/41897300/41897267/2e388edf.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)

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

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

Mt Holly

9.8/10

Exceptional

(36 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.

CA $356

CA $878 total

includes taxes & fees

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/f70a0c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/ef3ff692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/3b2bff89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/63000000/62960000/62953900/62953803/a4c7760d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 6 bed 7 Bath close to ski & shop w/ hot tub at Greybourne House in Manchester VT

[](https://www.expedia.ca/Manchester-Center-Hotels-6-Bed-7-Bath-VT-Retreat-Rent-A-Former-BB-Greybourne-House.h62953803.Hotel-Information)

Manchester Center

10/10

Exceptional

(51 reviews)

"Had a great time."

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

Neetesh B.

CA $1,340

CA $2,846 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Manchester-Center-Hotels-6-Bed-7-Bath-VT-Retreat-Rent-A-Former-BB-Greybourne-House.h62953803.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=2026-01-29&endDate=2026-01-30&regionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

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Aparthotels

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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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CONDO)

Apartments

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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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=CHALET)

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=2026-04-14&d1=2026-04-14&endDate=2026-04-17&d2=2026-04-17&lodging=VILLA)

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## Top Chester Hotel Reviews

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

### The Manchester View

10/10 Excellent

"Rooms were clean and they went above and beyond to check us in very early. I will definitely book again."

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

"Super friendly staff! Pool and hot tub were also a hit. Room was very clean and spacious, bath was clean! I'd return! "

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

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg)

### On The River Inn

10/10 Excellent

"Our stay was absolutely wonderful. The room was clean & comfortable with a nice view from balcony. The breakfast was good & the bar was very nice on a cold evening. Look forward to staying here again."

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

![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, nice pool and hot tub, and good price!"

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

![Bromley View Inn](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb_y.jpg)

### Bromley View Inn

10/10 Excellent

"Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!"

[](https://expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information)

![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg)

### The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Every thing was excellent "

[](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg)

### The Jackson 

10/10 Excellent

"Beautiful, quiet inn. We stayed Saturday through Tuesday after the holidyas, so it was especially quiet, just what we wanted. Staff was incredibly attentive and engaging, rooms were unique and comfortable. I highly recommend The Jackson. We will be returning in the spring to see the grounds!"

[](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.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

"Great staff"

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

![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/9c9da73f_y.jpg)

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

10/10 Excellent

"Very convenient location.! Spacious and clean room. "

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

## Find out more about Chester

## Chester Vacation Homes information

| Number of reviews | 395                |
| ----------------- | ------------------ |
| Accommodation     | 944 Vacation Homes |
| Lowest Price      | CA $424            |
| Highest Price     | CA $2,846          |

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