Title: 20 Best B&B in Chester, VT - Bed and Breakfast from $122 | 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

Next weekend

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

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

In one month

[Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

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

## Our top choices for Chester bed & breakfast

![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/450d23d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/7060d495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Room, Mountain View | Individually decorated, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/48815e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stone Hearth Inn and Eatery

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

Chester

9.2/10

Wonderful

(115 reviews)

"So great all around!"

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

Janet

$202 nightly

$221 total

Mar 10 - Mar 11

Total with taxes and fees

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

![Lounge](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/4ee226d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c0073409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/44151c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bromley View Inn

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

Bondville

9.0/10

Wonderful

(426 reviews)

"Clean room/ great breakfast"

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

Ryan

$111 nightly

$122 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/22815dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/81dd974d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/4bee0dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Colonel Williams Inn

[](https://www.expedia.com/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information)

Brattleboro

9.8/10

Exceptional

(349 reviews)

"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."

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

Sahand

$150 nightly

$166 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information)

![Porch](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/1e0ac20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/096e29dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/0ee737a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/c10f6d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harvest Barn Inn

[](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information)

Bellows Falls

9.8/10

Exceptional

(253 reviews)

"Everything was great. Awesome hosts, room, common areas and a fabulous breakfast. Can’t recommend too highly."

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

Mark

$147 nightly

$161 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/df603ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/d8604c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a625cff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/b858846d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Carriage Barn Inn

[](https://www.expedia.com/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information)

Keene

9.6/10

Exceptional

(169 reviews)

"Very helpful and welcoming host. "

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

Bruce

$148 nightly

$161 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information)

![Land view from property](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1023h453x0y0-571ad601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/b839bfbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dinner served, garden views ](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/24332bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/ea836d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Four Columns Inn

[](https://www.expedia.com/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information)

Newfane

9.8/10

Exceptional

(23 reviews)

"Everything was great 👍 I will stay there again and highly recommend to others "

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

Linda

$129 nightly

$141 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/b6d65569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/34f36e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (The Brighton Room) | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/abe8f80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/4c68c022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The One Cat B&B

[](https://www.expedia.com/Brattleboro-Hotels-The-One-Cat-BB.h13578971.Hotel-Information)

Brattleboro

9.6/10

Exceptional

(79 reviews)

"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"

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

Cara

$243 nightly

$268 total

Mar 6 - Mar 7

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-The-One-Cat-BB.h13578971.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/b9dbfee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/91483dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Jackson 

[](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

West Woodstock

9.6/10

Exceptional

(272 reviews)

"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."

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

Abby

$169 nightly

$186 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/5d6f68a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/ba818b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Room (Cinnamon) | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/e69208e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/cdc27f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Manchester

[](https://www.expedia.com/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information)

Manchester Village Historic District

10/10

Exceptional

(291 reviews)

"super cute and clean, felt like home after not living there for 4 years!"

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

MacLean

$165 nightly

$182 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/e4ab8f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/2bcff138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hot tub](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/84ff55dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/19942074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Gentian Lodge at Magic Mountain

[](https://www.expedia.com/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.Hotel-Information)

Londonderry

9.2/10

Wonderful

(115 reviews)

"Host was wonderful. "

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

Robert

$164 nightly

$181 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/0ba93825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/676cb54e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/2533d22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premier Room | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/2970ae6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Vesper 

[](https://www.expedia.com/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information)

Woodstock

9.2/10

Wonderful

(57 reviews)

"Charming bed and breakfast"

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

Nicholas

$163 nightly

$180 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information)

![Room, 1 Queen Bed, Garden View | Mountain view](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/ee964e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b590c7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Room, 1 King Bed | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/26455a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Cottage | Private kitchen](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/159c71cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windham Hill Inn

[](https://www.expedia.com/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information)

West Townshend

8.4/10

Very Good

(40 reviews)

"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."

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

J

$189 nightly

$206 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/53db29c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/b1b23979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/abd58cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/4d2bc29e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deer Brook Inn 

[](https://www.expedia.com/Woodstock-Hotels-Deer-Brook-Inn.h122648718.Hotel-Information)

Woodstock

$200 nightly

$220 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Woodstock-Hotels-Deer-Brook-Inn.h122648718.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/59f5ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/16188707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/5baffb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn on Putney Road

[](https://www.expedia.com/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information)

Brattleboro

9.8/10

Exceptional

(57 reviews)

"Room was super clean and the hosts are excellent. "

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

Joe

$235 nightly

$258 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576466/c4f8f589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576466/0097ab7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576466/a25acb34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576466/aed21581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Alpine 5, cozy Vermont retreat

[](https://www.expedia.com/Manchester-Center-Hotels-Alpine-5.h113576466.Hotel-Information)

Manchester

10/10

Exceptional

(1 review)

"We had a wonderful stay! The room was very clean and spacious, which made it extremely comfortable and relaxing. Everything was well maintained and exactly as described. The space felt fresh, organized, and welcoming from the moment we arrived.Overall, a great experience, and we would definitely stay here again. Highly recommend!"

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

Shuo P.

$119 nightly

$131 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Manchester-Center-Hotels-Alpine-5.h113576466.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/8cc0d819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 Queen Bed, Fireplace, Mountainside | Down comforters, individually decorated, individually furnished](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/e3012ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite | Down comforters, individually decorated, individually furnished](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/639c20cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deerfield Valley Inn

[](https://www.expedia.com/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information)

West Dover

9.4/10

Exceptional

(113 reviews)

"Great location Host Oz cooked up a great breakfast Room was fine for one person "

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

michael

$148 nightly

$163 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/487ff1a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/fa801882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/cc8097e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Big Bears Lodge

[](https://www.expedia.com/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information)

West Dover

9.0/10

Wonderful

(203 reviews)

"Great mom and pop motel minutes from Mount Snow"

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

Richard

$173 nightly

$190 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/d7baa23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Double Room, Courtyard View | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/ce0b45d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Suite, Garden View | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/4c69dfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Signature Double Room, Garden View | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/5423776f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay At Jimmy's

[](https://www.expedia.com/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information)

Woodstock

10/10

Exceptional

(48 reviews)

"Wonderful amenities, location, and team, Highly recommend and would love to stay again"

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

Heather

$256 nightly

$281 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/430958e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/dda7c041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/c2509b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Room, 1 King Bed, Fireplace, Mountain View | Bathroom | Separate tub and shower, jetted tub, designer toiletries, hair dryer](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/fb3063fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Ormsby Hill

[](https://www.expedia.com/Bennington-Hotels-The-Inn-At-Ormsby-Hill.h6025401.Hotel-Information)

Manchester Center

9.8/10

Exceptional

(156 reviews)

"Lovely place to stay Jack and Maryann excellent hosts"

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

Lenny

$246 nightly

$271 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Bennington-Hotels-The-Inn-At-Ormsby-Hill.h6025401.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/77eb994f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/0a80171b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/594556d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/1000000/900000/893700/893657/94881046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Echo Lake Inn

[](https://www.expedia.com/Ludlow-Hotels-Echo-Lake-Inn.h893657.Hotel-Information)

Plymouth

8.6/10

Excellent

(100 reviews)

"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "

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

Danielle

$230 nightly

$251 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Echo-Lake-Inn.h893657.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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## Top Chester Hotel Reviews

![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

"They allowed for early check-in, had a condo that slept 10 and my family was extremely comfortable"

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

"Friendly and helpful staff "

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

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Great room very clean"

[](https://expedia.com/Bennington-Hotels-Aspen-At-Manchester.h10254459.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

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

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

"Charming little motel. Rooms beautifully appointed. "

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

![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg)

### Kimpton Taconic Hotel by IHG

10/10 Excellent

"Hotel was lovely. Beautifully appointed. Staff was excellent and very helpful. "

[](https://expedia.com/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.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

"We loved our stay at the Black Bear! The check-in went smoothly with desk staff, Noah. She was very helpful and went over everything about our stay. The room was very clean. The hot tub was very nice and clean and a welcome after a day on the slopes. The shuttle to the mountain was great and ran frequently. The breakfast was always hot and had many options. We would definitely stay there again!"

[](https://expedia.com/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.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.com/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.com/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information)

## Find out more about Chester

## Chester B&B information

| Number of reviews | 2,766  |
| ----------------- | ------ |
| Accommodation     | 62 B&B |
| Lowest Price      | $122   |
| Highest Price     | $281   |

## Frequently asked questions

### What are the most popular Chester Bed and Breakfasts?

> For those planning a ski trip or family adventure, the Room in Historic Inn. 20 Minutes to Okemo. is a wonderful choice, rated 9.4\. It offers a cozy space with a well-appointed kitchenette and a charming porch to enjoy the fresh Vermont air. The location is ideal for both summer hiking and winter sports, ensuring that families can create lasting memories together in the great outdoors.
> 
>   
> Families will also appreciate the [Stone Hearth Inn and Eatery](https://www.expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information), which comes highly recommended with a score of 9.2\. Known for its delightful breakfast, including the famous blueberry French toast, this inn offers a warm and friendly space. With beautiful grounds for children to explore and easy access to nearby skiing and hiking, it's a great home base for adventure-seeking families.

### What is the nightly rate for a Bed & Breakfast in Chester?

### Are there any family-friendly B&Bs in Chester?

> For an equally family-friendly option, consider the Room in Historic Inn. Just 20 minutes from Okemo, this inviting space offers a sofa bed, making it great for families needing extra sleeping arrangements. It also includes a kitchenette and a microwave for those convenient snack time moments, along with a lovely patio to enjoy the fresh Vermont air.
> 
>   
> Another standout is the [Stone Hearth Inn and Eatery](https://www.expedia.com/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information), which truly caters to families. With a free buffet breakfast to start the day, children will love the selection of books and games available, along with complimentary cribs and highchairs. Its garden area provides a lovely outdoor space for kids to play while parents unwind. This property combines comfort and convenience, making it an excellent home base for family adventures in Chester.

### Which area is best to stay in a Chester B&B?

> Cultural experiences abound, with the historic Chester Village and its classic New England architecture just a short drive away. Visitors can enjoy local artisan shops and seasonal farmers' markets, superb for sampling regional produce and crafts. For a bit of fun, families can also venture to the nearby Magic Mountain Ski Area during winter months for skiing and snowboarding.
> 
>   
> For couples looking for a peaceful retreat, Chester Depot's scenic beauty is ideal. Stroll through the picturesque countryside or relax at one of the local cafes, soaking in the tranquil Vermont ambiance.

### When is the best time to book a B&B in Chester?

> July stands out as the busiest month, where you can join fellow travelers in enjoying the vibrant atmosphere. The area comes alive with family-friendly festivals and events, making it a great time for those seeking a lively and social experience. Whether you're interested in water sports on the lake or leisurely strolls through local shops, there's something for everyone.
> 
>   
> For travelers looking for a more budget-friendly option, consider visiting Chester in March. This month offers a quieter experience, where you can appreciate the serene beauty of the spring thaw. While the temperatures can be cooler, ranging from the low 30s to mid-50s Fahrenheit, it's a wonderful opportunity for those who enjoy a peaceful getaway and fewer crowds.

### What is the difference between a Chester B&B and a hotel?

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