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

Chester Hotel Guide - Family Friendly Hotels in Chester, Vermont

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Check availability on Chester Family Friendly Hotels

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chester family-friendly hotels

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.
A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.
A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.
A variety of dishes including a steak, muffins, and a dessert with fruit.

1. Fullerton Inn

Fullerton Inn
Chester Depot
€126
includes taxes & fees
9 Nov - 10 Nov
Fullerton Inn
A cozy room with a wooden table, a bean bag chair, a small white table, and a patterned rug.
A two-story house with a front porch, a garage, and a well-maintained lawn.
A wooden staircase leading to a door with a wreath, a potted plant, and a framed picture on the wall.
A hot tub in a forested area with a grill and a sign.

2. Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
€390
includes taxes & fees
1 Nov - 2 Nov
Historic 150-year-old farmhouse, Jacuzzi included
Dining
A two-story house with a front porch, a driveway, and autumn foliage.
Dining
A cozy living room with a sofa, armchair, and a glass coffee table. There are two windows with curtains, a fireplace, and a door leading to another room.

3. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
€364
includes taxes & fees
5 Nov - 6 Nov
Charming Chester Farmhouse near Near VT Slopes
A red wooden cabin with a balcony, surrounded by trees.
A two-story house with a deck, surrounded by dense forest.
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a white table and grey chairs.
A dining area with a table and chairs, a large arched window, and a view of a grassy landscape.

4. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
€894
includes taxes & fees
12 Oct - 13 Oct
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Room
Living area
Living area
Exterior

5. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
€630
includes taxes & fees
12 Oct - 13 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A bedroom with a bed, a nightstand, a dresser, a window with curtains, and a framed botanical illustration on the wall.
An aerial view of a residential area with houses, a tennis court, and a swimming pool.
A large two-story house with a front porch and a well-maintained lawn.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.

6. The Landgrove

The Landgrove
Londonderry
€196
includes taxes & fees
8 Nov - 9 Nov
The Landgrove
A modern bedroom with two beds, wooden headboards, a bench, a small table, and a large window with a view of greenery.
A modern bathroom with a large window, a black sink, a mirror, and a glass shower enclosure.
A living room with a sofa, a coffee table, a red chair, a lamp, and a patterned rug.
A person performing yoga on a wooden deck overlooking a river with trees in the background.

7. Otherland Hotel

Otherland Hotel
Newfane
€189
includes taxes & fees
1 Nov - 2 Nov
Otherland Hotel
A bedroom with a bed, dresser, TV, and a chair.
A panoramic view of a lake surrounded by forested hills.
A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.
A bathroom with a double sink, a large mirror, and a bed with a blue patterned bedspread.

8. Doveberry Inn

Doveberry Inn
West Dover
€119
includes taxes & fees
25 Oct - 26 Oct
Doveberry Inn
A hotel room with a large bed, a television, a desk with a lamp, a window with curtains, and a painting on the wall.
A Christmas tree decorated with lights, ornaments, and a bow.
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.

9. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
Londonderry
€99
includes taxes & fees
12 Oct - 13 Oct
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.
An indoor swimming pool with four chairs and a hot tub.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A spacious lobby with a fireplace, leather seating, and a chandelier.

10. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
€146
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort
View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"Room was adequate. Bedding was uncomfortable. We would not revisit this property. We would not recommend to others."
Bruce 4-night trip
Posted 1 hour ago
Pointe at Castle Hill Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice clean rooms comfortable, breakfast was a nice way to start today."
Alain 2-night trip
Posted 1 hour ago
The Black Bear Lodge at Stratton Mountain Resort
Latchis Hotel

Latchis Hotel

10/10 Excellent
"For being a historic hotel this place was nice. Sound machines in the rooms to make up for being on a busy street. Fan in the room to help with circulation. Historic charm in great walkable downtown location. Parking lot was small but there is additional parking in a city lot and on the street."
Jason 1-night trip
Posted 19 hours ago
Latchis Hotel
The Manchester View

The Manchester View

10/10 Excellent
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked goods was perfect and the Vermont coffee provided brought up to a higher level I can’t wait to go back for a longer stay"
Cathya 1-night trip
Posted 2 days ago
The Manchester View
Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 3 days ago
Colonial Motel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"Allen in the restaurant is great."
Bettina 1-night trip
Posted 5 days ago
Grand Summit Resort, A Vail Resorts Property
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 5 days ago
On The River Inn
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful location. Helpful staff"
Richard 1-night trip
Posted 12 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Frequently asked questions

What's Chester like for family-friendly holidays?
You may want to consider the relaxing destination of Chester if you've been thinking about a trip for the whole family. The chocolate shops, restaurants and hiking trails are just a few of the things that make this an attractive spot for a family holiday. Arrange a flight into Springfield, VT (VSF-Hartness State), which is the closest airport, or Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 25.4 mi (40.8 km) from the city centre.
What's the best family accommodation in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Chester?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What's there to see and do with your family in Chester?
While you are holidaying in Chester, you and the family may want to see some interesting spots such as DaVallia Art & Accents and Bonnie's Bundles Dolls. Make sure that you have lots of time for activities such as Vermont Country Store and Magic Mountain Ski Resort.