Find 4 Star Hotels in Chester, VT from $161

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 14 - Nov 15
Tomorrow
Nov 15 - Nov 16
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Our top choices for Chester 4-star hotels

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (631 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."
United States
Darrah
$369 nightly
The price is $406
Nov 30 - Dec 1
Total with taxes and fees
Woodstock Inn & Resort
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

2. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (343 reviews)
"Excellent stay"
United Kingdom
Richard
$176 nightly
The price is $194
Dec 1 - Dec 2
Total with taxes and fees
The Jackson
A spacious hotel lobby with a high ceiling, chandeliers, seating areas, and large windows.

3. The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (682 reviews)
"Very unique property with a feel like home feel Good breakfast ."
United States
Michael
$166 nightly
The price is $182
Nov 23 - Nov 24
Total with taxes and fees
The Equinox Golf Resort And Spa
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building.

4. Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (882 reviews)
"The Kimpton Taconic is a beautiful property with professional, friendly staff. We very much enjoyed our stay there and will stay there again the next time we are in Manchester VT."
United States
Jim
$216 nightly
The price is $238
Nov 18 - Nov 19
Total with taxes and fees
Kimpton Taconic Hotel by IHG
Two Adirondack chairs by a river with a forested hillside in the background.

5. On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place would stay again"
United States
Joseph
$149 nightly
The price is $163
Dec 6 - Dec 7
Total with taxes and fees
On The River Inn
A two-story building with a porch, American flag, and two white rocking chairs.

6. The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (401 reviews)
"Terrific place. Loved everything about it!"
United States
Jeffrey
$199 nightly
The price is $219
Nov 29 - Nov 30
Total with taxes and fees
The Reluctant Panther Inn and Restaurant
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (63 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
$148 nightly
The price is $161
Nov 23 - Nov 24
Total with taxes and fees
Four Columns Inn
A white building with a green roof and a stone wall in the foreground.

8. The Hermitage Inn Vermont

The Hermitage Inn Vermont
4.0 star property
West Dover
9.0 out of 10, Wonderful, (22 reviews)
"Could not have had a more perfect stay. Highly recommend."
United States
Steven
$371 nightly
The price is $408
Nov 25 - Nov 26
Total with taxes and fees
The Hermitage Inn Vermont
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

9. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (83 reviews)
"Breakfast was very good. Had dinner at the restaurant & it was excellent"
United States
Rula
$264 nightly
The price is $287
Nov 29 - Nov 30
Total with taxes and fees
The Inn at Weathersfield
A red building with a white roof, a golf cart, and a well-maintained lawn.

10. Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (29 reviews)
"Large unit - well laid out for three generation visit. Comfortable beds. Kitchen well appointed."
United States
Lori A.
Winterplace at Okemo, A Vail Resorts Property
A rustic lodge with stone walls, a stone fireplace, and outdoor seating.

11. Seesaw's Lodge

Seesaw's Lodge
4.0 star property
Peru
10.0 out of 10, Exceptional, (35 reviews)
"Check in and out was super easy - the room was beautiful and so clean. Was close to Manchester and Londonderry"
United States
Michaela
$240 nightly
The price is $262
Nov 15 - Nov 16
Total with taxes and fees
Seesaw's Lodge
An outdoor patio with tables and chairs, surrounded by lush greenery and string lights.

12. The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (105 reviews)
"Owners were very friendly. Food was incredible. Breakfast is included but they also have dinner available. Both were excellent. It was also nice having a small bar on site. Great place for a few drinks before we went out."
United States
Sam
The Village Inn of Woodstock
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

13. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (47 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
Windham Hill Inn
A large, multi-story building with a symmetrical facade, surrounded by a well-maintained lawn and wildflowers.

14. Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
4.0 star property
Clock Tower Base Area
7.8 out of 10, Good, (36 reviews)
"Great location!"
United States
DIEN
Solitude Village at Okemo by Vail Resorts
A traditional white building with black shutters, a stone pathway leading to the entrance, and a signboard advertising a breakfast buffet.

15. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
$267 nightly
The price is $294
Nov 15 - Nov 16
Total with taxes and fees
Inn on Putney Road
A grassy outdoor area with two Adirondack chairs under a tree, a small building, and a road in the background.

16. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
"Great stay"
United States
Wayne
$301 nightly
The price is $327
Nov 15 - Nov 16
Total with taxes and fees
Chesterfield Inn
A large, multi-story house with a snow-covered roof and multiple windows, surrounded by trees.

17. Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful four night stay at this great condo! Perfect if you are skiing out of Okemo! The condo was beautiful, clean and the host Bill was so communicative and responded to texts immediately. The gym and spa was also an added bonus! Great time! "
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
A bedroom with a large bed, a nightstand, a lamp, a window, and a painting on the wall.

18. The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (53 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B
A courtyard with a wooden staircase leading to a building entrance, surrounded by greenery and large rocks.

19. 'bearfoot Apres' Mtn-view Condo < 1 Mi to Mt Snow!

'bearfoot Apres' Mtn-view Condo < 1 Mi to Mt Snow!
4.0 star property
West Dover
'bearfoot Apres' Mtn-view Condo < 1 Mi to Mt Snow!
A wooden deck overlooking a swimming pool with a view of a forested area.

20. Bromley Mountain Escape w/ 2 Balconies: Hike & Ski

Bromley Mountain Escape w/ 2 Balconies: Hike & Ski
4.0 star property
Bromley Mountain
6.0 out of 10, (1 review)
"The property is low cost in a nice area of Peru seconds from Bromley Mtn. BUT the property needs some serious updating -No AC. The host was more than accomodating. "
United States
Chris
Bromley Mountain Escape w/ 2 Balconies: Hike & Ski

Top Chester Hotel Reviews

A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.
The Inn at Weathersfield

The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville

10/10 Excellent

Great Inn.
United States
Robert
Reviewed June 27, 2025
The Inn at Weathersfield

Find out more about Chester

The beginning of any much-needed holiday kicks off with selecting a location. Chester has been a popular destination with tourists because it offers so much. Yet, "location, location, location" applies to more than just what city where your plane lands. Now that you have a feeling for the area, it is time you to learn a little more about your new digs.

Properties as Picturesque as Chester

Chester saw its fair share of visitors this past year. Our review section provides reviews that highlight how astounding these rooms are. The hotels found here strive to make your vacation as pleasant as your evenings exploring Chester. These hotels work to make the facilities and grounds hospitable from the minute you step out of your car. You won't need to venture far to keep up with your workout schedule, enjoy a refreshing plunge, or find a nice meal during your stay with everything they provide.

Rooms have been configured to keep your utmost comfort in mind, with amenities like premium bedding, and in-room tea or coffee, and designer bathroom products. So, lay back and decompress. Moreover, if you find yourself in need of anything further, you can trust the staff will try their best to ensure you remain pleased during your time there. These properties are so nice that you'll regret the day you have to leave.

Book a 4-Star Hotel in Chester Today!

A vacation to Chester should be one where you won't have to be concerned about the little things. Of course, your getaway should be all about getting the most out of your destination. And getting the most means giving yourself the very best. Expedia has 4-star hotels that allow you to do just that. Book through Expedia today!

Frequently Asked Questions

How much does it cost to stay in a 4-star hotel in Chester?

With Expedia's handy search filters, bagging a terrific deal on a 4-star hotel in Chester just got simpler. Start by keying in your chosen arrival date and length of your break. Then sort the results by price and pick a hotel that best fits your style and budget.

  • Search for the lowest price from $161

What's the difference between 5-star and 4-star hotels in Chester?

Offering an inviting traveler experience and upscale décor, 4-star hotels are a great option for your Chester trip. These kinds of accommodations generally feature lots of handy amenities that make it easy to unpack and unwind — think 24-hour room service, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to indulge you in exclusive perks and amenities. On-site health clubs, complimentary toiletries and gourmet dining are typically included at these deluxe retreats.

Does Chester have any 4-star all-inclusive resorts?

Use our "All inclusive" filter to find your next dream getaway in Chester where just about everything is taken care of, from your accommodations to your meals, activities and entertainment. We can also help you find standard 4-star stays in and around this destination.

Are there any 4-star casino hotels in Chester?

Use our convenient filters to narrow down your Chester search by star rating, amenities and much more. Whether you're after the complete casino resort experience or just want to try your luck while living it up in 4-star style, you're sure to find a place that strikes the perfect balance between relaxation and entertainment.

Explore a world of travel with Expedia