Holiday Homes in Chester

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Check prices for these dates

In two weeks
19 June - 21 June
In two months
31 July - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Chester holiday homes

Exterior

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is AU$797
includes taxes & fees
2 June - 3 June
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (20 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is AU$560
includes taxes & fees
14 June - 15 June
Charming Chester Farmhouse near Near VT Slopes
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AU$1,380
includes taxes & fees
8 June - 9 June
Cozy Vermont Cabin · Mountain Views · Near Okemo
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (60 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AU$442
includes taxes & fees
2 June - 3 June
Family Friendly Hilltop House In Putney Vermont
Interior

Perfect 2-bedroom in charming Newport

Perfect 2-bedroom in charming Newport
Newport
The price is AU$312
includes taxes & fees
15 June - 16 June
Perfect 2-bedroom in charming Newport
Fridge, microwave, oven, stovetop

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AU$661
includes taxes & fees
4 June - 5 June
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Smart TV, fireplace, video games, books

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

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is AU$738
includes taxes & fees
14 June - 15 June
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AU$469
includes taxes & fees
2 June - 3 June
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 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
Ann R.
The price is AU$703
includes taxes & fees
2 June - 3 June
Lakefront Family Fun Retreat
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"Couldn’t have picked a better place! Warm and comfy and sooo close to okemo "
United States
Erica B.
The price is AU$469
includes taxes & fees
2 June - 3 June
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is AU$1,080
includes taxes & fees
3 June - 4 June
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Exterior detail

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
9.6 out of 10, Exceptional, (29 reviews)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
The price is AU$1,223
includes taxes & fees
9 June - 10 June
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Exterior

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

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Jamaica
9.6 out of 10, Exceptional, (26 reviews)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
United States
Chris M.
The price is AU$1,106
includes taxes & fees
2 June - 3 June
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Dining

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
Dover
10.0 out of 10, Exceptional, (26 reviews)
"The hosts were very responsive, accommodating, and our family had a wonderful stay! "
United States
caroline m.
The price is AU$581
includes taxes & fees
4 June - 5 June
Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
Smart TV, fireplace, books

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Dover
10.0 out of 10, Exceptional, (9 reviews)
"We had a great family ski trip and stay in this cozy house. Good location close to town and was the perfect setup up to accommodate our two families of four. Beth and Jason were very responsive and easy to communicate with, would highly recommend! "
United States
James D.
The price is AU$834
includes taxes & fees
3 June - 4 June
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.0 out of 10, Very good, (2 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Winhall
9.4 out of 10, Exceptional, (38 reviews)
"Our family had a wonderful time staying in this home."
United States
Meghan C.
The price is AU$911
includes taxes & fees
2 June - 3 June
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Property grounds

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 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
Owen C.
The price is AU$770
includes taxes & fees
3 June - 4 June
Large Killington Area Home | Sleeps 7 | Game Room
Microwave, oven, stovetop, dishwasher

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts

3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Richville
The price is AU$501
includes taxes & fees
8 June - 9 June
3BR Family Home in Manchester, VT -Near Downtown, Outlets & Ski Resorts
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is AU$835
includes taxes & fees
3 June - 4 June
New Ludlow Village Home with Stunning Okemo Mountain View
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"My family all stayed at The Hampton Inn of Manchester for my husband’s nephew’s wedding. The rooms were clean and comfortable and the staff was very accommodating to what our needs were for the weekend. The breakfast station was fantastic as we could all enjoy breakfast with each other without going anywhere else and making reservations for a big group breakfast. I would recommend anyone visiting Manchester, Vermont to checkout the Hampton Inn for their stay. They won’t be disappointed. Remember to bring your bathing suit to take a dip in the indoor pool. We forgot as our stay was for a weekend wedding but will remember for our next visit."
Margaret 2-night trip
Posted 3 hours ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester Holiday Homes information

Number of reviews
367
Accommodation
966 Holiday Homes
Lowest Price
AU$312
Highest Price
AU$1,380