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

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Check availability on Chester Family Hotels

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chester family-friendly hotels

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.
A living room with a fireplace, two armchairs, a TV mounted above the fireplace, and a desk with a mirror and lamp.
A room with a red sofa, armchairs, a coffee table, and a fireplace. There is a window with a view of trees and a chandelier.
A stone facade with a wooden door, steps leading up to a porch, and a small white chair outside.

1. The Hartness House

The Hartness House
Springfield
￥32,691
￥35,961 total
includes taxes & fees
Oct 22 - Oct 23
The Hartness House
A red house with a covered porch and a chimney.
A kitchen with a wooden table and chairs, a microwave, and cabinets.
A kitchen with white cabinets, a microwave, a stove, and a sink.
A living room with a wood-burning stove, a blue armchair, and a bookshelf.

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
  • Renovated schoolhouse cabin offers tranquil family time with hiking trails and children's books.
￥26,767
￥58,370 total
includes taxes & fees
Sep 30 - Oct 1
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A cozy lounge area with comfortable seating, a billiards table, and a decorated Christmas tree.
A multi-story hotel with balconies, a ski slope in the background, and a clear blue sky.
A hotel room with a bed, a chair, a table, and a view of mountains through a large window.
A group of people sitting around a circular fire pit in a snowy outdoor setting.

3. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
  • Family fun at this ski-in/ski-out lodge offers game room adventures, mountain access, and recently renovated spaces.
￥21,390
￥23,529 total
includes taxes & fees
Oct 1 - Oct 2
Sun Lodge near Manchester VT, Ascend Collection Hotel
Two children playing with wooden blocks in a room with a carpeted floor, a brown leather couch, and a wooden table with chairs.
A circular seating arrangement with Adirondack chairs around a central fire pit, set on a gravel area with a grassy field and trees in the background.
A cozy restaurant with wooden tables and chairs, a kitchen area, and a 'GATHER' sign on the wall.
A rustic lodge with a covered parking area and a mountain backdrop.

4. Aerie Inn of Vermont

Aerie Inn of Vermont
East Dorset
  • Family fun awaits in the mountains with easy lake access, outdoor playground, and cozy firepit for evening entertainment.
￥17,236
￥18,787 total
includes taxes & fees
Sep 28 - Sep 29
Aerie Inn of Vermont
A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.
A spacious living room with wooden beams, a patterned sofa, a yellow armchair, and a red door.
A house with a red exterior, large windows, and a well-maintained garden with various plants and flowers.
A cozy living room with a fireplace, wooden furniture, and large windows.

5. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
  • Adventure awaits at this family-friendly lodge where breakfast is included and Magic Mountain Ski Resort is just a short drive away.
￥32,309
￥35,217 total
includes taxes & fees
Sep 27 - Sep 28
COHO Inn & Motor Lodge
A claw machine arcade with plush toys inside, a blue and yellow vending machine, and a steering wheel control panel.
A lobby with a stone fireplace, leather sofas, and a reception desk.
A stone wall surrounding a swimming pool with a metal handrail.
A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a door leading to another room.

6. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
  • Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
￥21,802
￥26,379 total
includes taxes & fees
Sep 28 - Sep 29
The Black Bear Lodge at Stratton Mountain Resort
A bedroom with a bed, a nightstand, a dresser, a window with curtains, and a framed botanical illustration on the wall.
A large two-story house with a front porch and a well-maintained lawn.
A cozy interior with a bar area, wooden furniture, and a Christmas tree.
A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.

7. The Landgrove

The Landgrove
Londonderry
￥34,430
￥37,529 total
includes taxes & fees
Oct 4 - Oct 5
The Landgrove
A grassy field with a playground and trees in the background.
A compact hotel room with a dark wooden desk, a chair, a small kitchenette, and a flat-screen TV.
A motel with a parking lot, a covered walkway, and a staircase leading to the entrance.
A hotel room with two beds, a desk, and a TV.

8. The Putney Inn

The Putney Inn
Putney
  • Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
￥13,318
￥14,650 total
includes taxes & fees
Oct 25 - Oct 26
The Putney Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
A spacious living area with a staircase, a red door, and a large window.
A serene pond with a statue in the center, surrounded by lush greenery and trees.
A living room with leather sofas, a round ottoman, a fireplace, and a bookshelf.

9. Four Columns Inn

Four Columns Inn
Newfane
￥23,298
￥25,395 total
includes taxes & fees
Sep 29 - Sep 30
Four Columns Inn
A room with a flat-screen TV mounted on the wall, a bean bag chair, a small table with chairs, and a play area with colorful toys.
A bar area with stools, a counter, and a large window offering a view of a snowy landscape.
A group of people gathered around a fire pit in a snowy outdoor setting with a large building in the background.
A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.

10. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
￥28,330
￥33,491 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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

The Manchester View

The Manchester View

10/10 Excellent
"Very cool unique setting and property. The bed was like a cloud and very relaxing."
David B 1-night trip
Posted 22 hours ago
The Manchester View
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 1 day ago
The Equinox Golf Resort And Spa
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 2 days ago
Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very nice stay and nice rooms."
Nicole 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
Latchis Hotel

Latchis Hotel

10/10 Excellent
"WE enjoyed the architecture of the whole complex - reception coffee lounge (Hot Drinks day and night as a compliment). Parking was right there. Center of town. The staff helped us when we needed to extend at the special rate. It attracts fun guests. It is a special place - not the run of the mill franchise. The linen is first class, nice thick towels. The room had a microwave and a refrig, plus the record player theme is another theme for folks who appreciate the vinyl era. Remember - Art Deco Era - not modern era."
Kris 6-night trip
Posted 3 days ago
Latchis Hotel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

8/10 Good
"The pool was not available due to repair. The parking was limited (we had to walk up/down the hill to overflow parking). The faucet in our room made machine gun noise. The room was pretty big and clean. Deli was good. The restaurant bartender was very helpful. The shuttle bus service was great."
Hisayo 2-night trip
Posted 4 days ago
Grand Summit Resort, A Vail Resorts Property
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 6 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
"Absolutely beautiful location. Everything was perfect."
Shannon 4-night trip
Posted 6 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Na"
Maria 1-night trip
Posted 9 days ago
The Shire Woodstock

Frequently asked questions

What's Chester like for family-friendly vacations?
You might 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 vacation. 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 center.
What's the best place to stay for a family vacation 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 vacation in Chester?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What's there to see and do with your family in Chester?
While you are vacationing in Chester, you and the family might want to see interesting spots such as Bonnie's Bundles Dolls and DaVallia Art & Accents. Make sure you have lots of time for activities like Vermont Country Store and Magic Mountain Ski Resort.

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