Find kid-friendly hotels & resorts in Chester, VT from $103

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Top Chester Family Hotels

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1000)
"Very enjoyable stay"
$94 nightly
The price is $103
Oct 26 - Oct 27
Total with taxes and fees
The Putney Inn

Claremont Motor Lodge

2.5 star property
8.8 out of 10, Excellent, (406)
"Great place to stay"
$114 nightly
The price is $124
Oct 8 - Oct 9
Total with taxes and fees
Claremont Motor Lodge

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (603)
"Great place!"
$152 nightly
The price is $165
Oct 27 - Oct 28
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (96)
"Sweet place to stay"
$311 nightly
The price is $340
Oct 6 - Oct 7
Total with taxes and fees
Stone Hearth Inn and Eatery

Historic 150-year-old farmhouse, Jacuzzi included

9.8 out of 10, Exceptional, (7)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
$418 nightly
The price is $468
Nov 2 - Nov 3
Total with taxes and fees
Historic 150-year-old farmhouse, Jacuzzi included

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
$149 nightly
The price is $167
Nov 2 - Nov 3
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn

King & Queen Suite in Historic Inn Circa 1780

9.8 out of 10, Exceptional, (16)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
$304 nightly
The price is $340
Oct 5 - Oct 6
Total with taxes and fees
King & Queen Suite in Historic Inn Circa 1780

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very Good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
$144 nightly
The price is $161
Nov 2 - Nov 3
Total with taxes and fees
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
$215 nightly
The price is $241
Oct 6 - Oct 7
Total with taxes and fees
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very Good, (1004)
"Would definitely stay again. Very convenient location "
$152 nightly
The price is $165
Nov 2 - Nov 3
Total with taxes and fees
Best Western Plus Keene Hotel
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.

Find out more about Chester

Find out more about Chester

Family friendly things to do in Chester

Chester, Vermont, offers a delightful blend of family-friendly activities that ensure everyone has a memorable getaway. Start your adventure at the picturesque Green Mountain National Forest, where families can hike on scenic trails, enjoy picnics, and even spot wildlife. The nearby Magic Mountain Ski Area is perfect for winter fun, with skiing and snowboarding options suitable for all skill levels – making it a great spot for families to learn together. For a splash of culture, visit the historic Chester Village, where you can explore charming shops and eateries, or stop by the local farmers' market to sample fresh produce and artisan goods. Don't miss the unique experience of the nearby Grafton Village Cheese Company, where kids can watch cheese-making demonstrations and taste delicious local cheeses. When it comes to accommodations, the area offers family-friendly hotels that ensure comfort and convenience, often featuring spacious rooms and amenities like pools and breakfast options. Staying in Chester not only places you at the heart of these activities but also allows your family to unwind in a peaceful, scenic environment after a day of adventure.

Find the best family friendly hotels in Chester

Chester, Vermont offers a warm and welcoming environment for families seeking adventure and comfort. Here are some top hotels that cater to family-friendly needs, ensuring a delightful stay for both parents and children.

King & Queen Suite in Historic Inn Circa 1780

  • Why it's great for a family-friendly adventure: The King & Queen Suite in this historic inn is a wonderful option for families, showcasing an excellent guest review rating of 9.6. This suite offers a kitchen and kitchenette, providing families with the flexibility to prepare their own meals. The addition of games for children ensures that younger guests are entertained during their stay.
  • Other amenities: Guests will appreciate the outdoor patio, perfect for relaxation after a day of exploration. The inn is conveniently located near skiing and hiking activities, making it an excellent choice for active families. Additional amenities include air conditioning, onsite parking, and dining options, creating a comfortable and enjoyable family getaway.
  • Neighborhood: Chester Depot
  • Nearby attractions: DaVallia Art & Accents - 0.09 miles, Bonnie's Bundles Dolls - 0.76 miles

Room in Historic Inn! 20 Minutes to Okemo!

  • Why it's great for a family-friendly adventure: This charming room in a historic inn offers a cozy retreat with a guest review rating of 9.2, making it a great choice for families. The room features a kitchenette, allowing for convenient meal preparation, while a sofa bed provides extra sleeping space for children. The inviting atmosphere ensures families feel at home during their stay.
  • Other amenities: Located just 20 minutes from Okemo, this inn offers easy access to skiing and outdoor activities. Families can enjoy the patio for outdoor relaxation, and nearby shopping and winery tours provide additional entertainment options. Other features include air conditioning, onsite parking, and a microwave, catering to all family needs.
  • Neighborhood: Chester Depot
  • Nearby attractions: DaVallia Art & Accents - 0.09 miles, Bonnie's Bundles Dolls - 0.76 miles

Stone Hearth Inn and Eatery

  • Why it's great for a family-friendly adventure: Stone Hearth Inn and Eatery is an ideal choice for families, a strong guest review rating of 9.2. With a variety of amenities designed for children, including free cribs and highchairs, this charming inn ensures that guests of all ages feel at home. The complimentary buffet breakfast is perfect for fueling up before a day of exploration in the beautiful Vermont landscape.
  • Other amenities: In addition to its family-friendly amenities, Stone Hearth Inn offers a picturesque garden where children can play and explore. Guests can enjoy nearby skiing, snowboarding, and sledding opportunities, making it an exciting destination year-round. Other amenities include air conditioning, free toiletries, and easy self-parking, providing convenience and comfort throughout your stay.
  • Nearby attractions: DaVallia Art & Accents - 1.28 miles, Bonnie's Bundles Dolls - 1.71 miles

Top Chester Hotel Reviews

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 DaVallia Art & Accents and Bonnie's Bundles Dolls. Make sure you have lots of time for activities like Vermont Country Store and Plummer's Sugar House.

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