A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check availability on Chester Golf Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Chester hotels with a golf course

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.
A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.
A Christmas tree decorated with lights, ornaments, and a bow.
A bar area with a sign reading "MAGIC" and "featured Vermont beers".

1. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
United States
Terry
CA $132
CA $152 total
includes taxes & fees
Oct 19 - Oct 20
The Upper Pass Lodge at Magic Mountain
A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.
A spacious lobby with a fireplace, leather seating, and a chandelier.

2. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
CA $216
CA $247 total
includes taxes & fees
Oct 28 - Oct 29
Pointe at Castle Hill Resort
A bedroom with a fireplace, two beds, a chair, and a nightstand.
A green building with a wooden deck, a small porch, and a sign that reads 'Motel.'
A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.
A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.

3. The Manchester View

The Manchester View
Manchester Center
United States
Jan
CA $144
CA $158 total
includes taxes & fees
Nov 3 - Nov 4
The Manchester View
A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.
A group of people sitting around a circular fire pit in a snowy outdoor setting.
A multi-story hotel with balconies, a ski slope in the background, and a clear blue sky.
A bar area with wooden ceiling, shelves with bottles, and a bar counter.

4. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Lynn
CA $169
CA $185 total
includes taxes & fees
Nov 9 - Nov 10
Sun Lodge near Manchester VT, Ascend Collection Hotel
A golf course with rolling hills, trees, and a distant mountain range.
A hotel with a swimming pool area, including two hot tubs and lounge chairs.
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A couple standing on a balcony with a view of a hotel courtyard.

5. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Mst M
CA $275
CA $334 total
includes taxes & fees
Oct 27 - Oct 28
Jackson Gore Village, A Vail Resorts Property
A multi-story hotel with a central courtyard and a reflective water feature.
A bar area with stools, a counter, and a large window offering a view of a snowy landscape.
A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.
A group of people gathered around a fire pit in a snowy outdoor setting with a large building in the background.

6. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
CA $196
CA $237 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A large stone building with a steep roof, surrounded by dense forest and hills.
A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.
A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.
A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

7. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
CA $316
CA $344 total
includes taxes & fees
Oct 27 - Oct 28
Castle Hill Resort And Spa
A lobby with a stone fireplace, leather sofas, and a reception desk.
A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.
A bathroom with a shower, a sink, and a mirror.
A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a door leading to another room.

8. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
United States
Joseph
CA $192
CA $232 total
includes taxes & fees
Oct 18 - Oct 19
The Black Bear Lodge at Stratton Mountain Resort
A red house with a covered porch and a chimney.
A living room with a wood-burning stove, a blue armchair, and a bookshelf.
A kitchen with white cabinets, a microwave, a stove, and a sink.
A kitchen with a wooden table and chairs, a microwave, and cabinets.

9. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
CA $240
CA $526 total
includes taxes & fees
Oct 20 - Oct 21
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A two-story building with a patio area featuring outdoor seating and a stone fire pit.
A hotel with a covered entrance, a flagpole with an American flag, and a brick building with multiple windows.
A swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.
A spacious living area with a fireplace, comfortable seating, and a stone accent wall.

10. Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester
Manchester Center
United States
Rosemary
CA $215
CA $237 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Inn and Suites Manchester
View all properties

Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

8/10 Good
"Breakfast could have been better, more healthly foods"
Angelena 2-night trip
Posted 8 hours ago
Hampton Inn and Suites Manchester
Colonial Motel

Colonial Motel

10/10 Excellent
"Value for money. Clean and conveniently located. Friendly staff."
Swaraj 2-night trip
Posted 11 hours ago
Colonial Motel
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Great resort. Only negative was that our bed was a murphy bed, mattress not the best, with no night stands. Everything else was good"
Rafael Jose 1-night trip
Posted 13 hours ago
Jackson Gore Village, A Vail Resorts Property
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"Ij kii it"
Kevin 2-night trip
Posted 21 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Manchester View

The Manchester View

10/10 Excellent
"Staff was so sweet and accommodating and we really enjoyed the delicious breakfast in the morning. We will definitely return!"
Janee 1-night trip
Posted 2 days ago
The Manchester View
Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Great location, simple room--minimalist but nice with microwave, fridge. Was a great place to set up headquarters for our trip to Vermont. Beautiful view behind the motel with firepits. It is a self-serve kind of property, which suited us well. We stayed 4 days and they didn't come to clean throughout. But we could go to the office and pick up anything we needed: extra toiletries, towels, etc. We enjoyed staying at the Aspen."
Sarah 4-night trip
Posted 3 days ago
Aspen At Manchester
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Good"
Kenton 2-night trip
Posted 4 days ago
The Equinox Golf Resort And Spa
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"It's a great place to stay! I've been there several times in different seasons. Off-season or leaf peeper season the free breakfast is a lot less than the free breakfast during ski season. During ski season AKA winter, eggs, waffles, pancakes etc however during other seasons they only offer cold cereal, milk bagels toast and juice and coffee of course. Other than that it's a fantastic place and they're dog friendly"
Bridget 1-night trip
Posted 6 days ago
The Black Bear Lodge at Stratton Mountain Resort
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 11 days ago
On The River Inn

Frequently asked questions

Are you looking for a golf hotel in Chester?
From golf lessons to driving ranges to mini golf, Expedia has something for you. Check out the mountain views in Chester - worth a picture or two! Enjoy the shopping and coffeehouses during your vacation.
How many golf hotels are there in Chester?
Expedia has 1 accommodation option in Chester classified as a golf hotel.
What should I see and do in Chester while on a golf vacation?
When you're ready for a break from the links, you'll discover that Chester has lots to offer. Explore the local sights and attractions with a stop at DaVallia Art & Accents and Bonnie's Bundles Dolls.
What is a golf hotel in Chester like?
Golf hotels in Chester offer guest rooms as well as convenient access to a golf course. On Expedia, you will be able to find golf hotels with either a 9+ hole golf course, or that are located next to an 18+ hole golf course. Golf hotels provide a selection of services and amenities such as golf club rentals, clubhouses, and golf shuttles.

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