Title: The Best Chester, VT Chalets from $407 | Expedia.com

[Chester Travel Guide](https://expedia.com/Chester.dx89014)[Hotels in Chester](https://expedia.com/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[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)

![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

## 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 chalets

![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/26cdcbb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/341be75e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/7665cd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

[](https://www.expedia.com/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information)

Dover

9.8/10

Exceptional

(25 reviews)

"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "

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

SZU YIN C.

$382 nightly

$432 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/a3e005f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/6a20b4d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/407a0d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/f3293a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Vermont Mountain Escape | Hot Tub Sauna EV

[](https://www.expedia.com/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information)

Jamaica

10/10

Exceptional

(3 reviews)

"Great peaceful stay. Hosts were always in communication with us. Close to Stratton. Hot tube & sauna were a great top off to a day of skiing. "

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

fran g.

$774 nightly

$823 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/b3ddab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet Mount Snow/Stratton Skiing/hiking

[](https://www.expedia.com/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

East Dover

9.8/10

Exceptional

(10 reviews)

"Easy to find! Clean! Cozy!! Would definitely stay again! "

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

Roy-michael G.

$360 nightly

$407 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/cc65421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/31c838bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/83acf129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/aaebfa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private cabin: 7 mins to slopes, wood fireplace

[](https://www.expedia.com/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information)

Dover

9.8/10

Exceptional

(8 reviews)

"The host - Excellent communication and very accommodating!"

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

Erika O.

$440 nightly

$497 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/eda7773c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/ec10883e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/e051b2f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/f7ab718d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

[](https://www.expedia.com/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information)

Wardsboro

10/10

Exceptional

(19 reviews)

"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"

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

Joseph R.

$365 nightly

$412 total

Apr 22 - Apr 23

Total with taxes and fees

[](https://www.expedia.com/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/76d2f10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/accd446a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/3a0b064f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/f158318f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

[](https://www.expedia.com/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information)

Dover

10/10

Exceptional

(12 reviews)

"Doug was very communicative and the home was beautiful!"

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

Kate M.

$650 nightly

$735 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/6da0ce7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/3bd9f0bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/526de6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/d54b3197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

[](https://www.expedia.com/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information)

Wardsboro

10/10

Exceptional

(7 reviews)

"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."

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

Kristen T.

$444 nightly

$502 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/5f637af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/dcc44385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/38bc7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/4c3f61c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

[](https://www.expedia.com/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information)

Dover

10/10

Exceptional

(17 reviews)

"This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. "

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

Kaymari T.

$630 nightly

$712 total

Apr 6 - Apr 7

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/d74e8c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/fdf153b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/6bb1cc24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/deccb16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

[](https://www.expedia.com/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

Stratton

10/10

Exceptional

(6 reviews)

"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "

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

Nicholas D.

$640 nightly

$723 total

Apr 20 - Apr 21

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/0d4d95fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/33af9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/97a2d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/w2180h1456x4y0-3d3ff46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW Private Chalet - 4 mins to Mt Snow

[](https://www.expedia.com/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information)

Dover

10/10

Exceptional

(3 reviews)

"Great place close enough to everything you need but set off the road for quiet evenings. Clean, spacious open floor plan great accommodation that checks all the needs for a ski getaway. "

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

Mark C.

$581 nightly

$657 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1071x0y2-62744863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1076x0y4-eec2a42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/84b8211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1070h1076x5y0-75daf8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

[](https://www.expedia.com/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information)

Dover

10/10

Exceptional

(7 reviews)

"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "

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

Chris I.

$878 nightly

$992 total

Apr 9 - Apr 10

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.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.

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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Cottages

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Condos

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Aparthotels

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Apartments

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Chalets

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Villas

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## Top Chester Hotel Reviews

![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)

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

### Pointe at Castle Hill Resort

10/10 Excellent

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

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

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

### The Covered Bridge Inn

6/10 Okay

"Good job"

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

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

### On The River Inn

10/10 Excellent

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

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

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

### Best Western Plus Keene Hotel

4/10 Poor

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

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

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

### Colonial Motel And Spa

2/10 Terrible

"What a dump"

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

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

### Hideaway Inn Mt. Snow

6/10 Okay

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

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

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

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

10/10 Excellent

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

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

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

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

4/10 Poor

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

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

## Find out more about Chester

## Chester Chalets information

| Number of reviews | 117         |
| ----------------- | ----------- |
| Accommodation     | 102 Chalets |
| Lowest Price      | $407        |
| Highest Price     | $992        |

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