Choose from 64 vacation rentals located in Chester, Vermont. Top filters in Chester include Internet / Wifi, Parking, and Kitchen or Kitchenette. Prices range from R1,341 to R18,911 per night. Our most popular vacation rental types near Chester are Hotel and RV.

Top vacation rentals in Chester

Outdoor dining
10.0
Outstanding(196 Reviews)
Vermont Hillside Cottage w/Great View - Pet Friendly
House
 in Chester
4 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette

This House for R 2,502 in Chester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

RRRR
vrbo logo
View deal
Start earning One Key rewards
Interior
9.7
Outstanding(70 Reviews)
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Cabin
 in Chester
5 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen or Kitchenette

The best choice in Chester for Cabin, for R 4,522 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

RRRR
vrbo logo
View deal
Photo of the whole room
9.6
Outstanding(7 Reviews)
Inn Victoria
Inn
 in Chester
1 king bed, 1 full bed
Garden · Kitchen or Kitchenette · Air conditioner

This inviting Inn in Chester can fit your needs for many types of vacations, at R 3,337 per night.

RRRR
booking logo
View deal
Property view
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
 in Chester
Pets allowed · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Chester in our House, Chester Farmhouse on 100 Acres, 15 Min to Okemo!. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.

RRRR
booking logo
View deal

Vacation rentals with internet & wifi in Chester

Dining
9.6
Outstanding(47 Reviews)
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
House
 in Chester
10 guests · 6 bedrooms · 2 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner

This attractive House in Chester, R 5,613 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

RRRR
vrbo logo
View deal
TV, fireplace, video-game console, DVD player
9.9
Outstanding(39 Reviews)
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!
House
 in Chester
9 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Internet / Wifi

Indulge in a peaceful retreat at Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!, our elegant House in Chester. Enjoy amenities including Dishwasher, Fireplace and Internet / Wifi, and more.

RRRR
vrbo logo
View deal
Property building, Garden
8.4
Excellent(70 Reviews)
Stone Hearth Inn and Eatery
Bed and Breakfast
 in Chester
1 queen bed
Garden · Internet / Wifi · Parking

Are you ready to indulge in a relaxing getaway? Our Bed and Breakfast in Chester has everything you need for a rejuvenating stay. Treat yourself to Stone Hearth Inn and Eatery's exceptional amenities, such as Fireplace, Internet / Wifi and Parking.

RRRR
booking logo
View deal
Property view
8.1
Excellent(78 Reviews)
Chester Inn
Inn
 in Chester
2 king beds, 1 futon
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Inn in Chester has everything you need for a rejuvenating stay. Treat yourself to Chester Inn's exceptional amenities, such as Air conditioner, Fireplace and Internet / Wifi.

RRRR
booking logo
View deal
city photo
Chester

Chester travel guide

Let us help you plan your perfect Chester vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chester, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Chester?

  • Internet / Wifi
  • Parking
  • Kitchen or Kitchenette

What are the must-visit tourist attractions in Chester, VT?

Chester, VT is a quaint and picturesque town that offers a variety of tourist attractions. The must-visit attractions include the Chester-Andover Family Center, the Chester Historical Society, the Chester Green, and the Farrar-Mansur House.

  • Chester-Andover Family Center
  • Chester Historical Society
  • Chester Green
  • Farrar-Mansur House

How can I get around in Chester, VT?

You can get around Chester, VT in a variety of ways:

  • Car or motorcycle
  • Bicycle
  • Public transportation

The town also offers rideshare programs like Uber and Lyft to get around.

Where can I find affordable accommodation in Chester, VT?

Chester, VT offers a variety of affordable accommodation options. Here are a few of the top choices:

  • The Inn at Weston: A charming inn located in the heart of Weston, VT, offering a variety of rooms and suites.
  • The Chester House Inn: A cozy bed and breakfast located in the heart of town, offering comfortable and affordable lodging.
  • The Chesterfield Inn: A historic inn located on the banks of the Connecticut River, offering a variety of rooms and suites.
  • The Black Bear Inn: A rustic inn located in the heart of town, offering a variety of rooms and suites.

No matter what type of accommodation you're looking for, there's something for everyone in Chester, VT.

What is the culture like in Chester, VT?

Chester, VT is a small town located in the Green Mountains of Vermont. It is a vibrant community with a unique culture that is rooted in the history of the area. Here are 5 aspects of the culture in Chester, VT:

  • The town celebrates its history through its annual Chester Festival
  • The town is home to a variety of artists, musicians, and writers
  • The town has a strong sense of community and support for local businesses
  • The town has a variety of outdoor activities such as skiing, snowshoeing, and hiking
  • The town has a vibrant food scene with a variety of restaurants and food trucks

Is Chester, VT safe to travel to?

Chester, VT is generally considered safe to travel to. Here are some safety tips to keep in mind when visiting:

  • Be aware of your surroundings
  • Avoid walking alone at night
  • Keep valuables out of sight

What are the popular shopping destinations in Chester, VT?

The popular shopping destinations in Chester, VT are:

  • The Chester Village Store
  • Chester General Store
  • Chester Antiques Mall

What are the best neighborhoods to visit in Chester, VT?

The best neighborhoods to visit in Chester, VT are:

  • Downtown - a vibrant area with plenty of shops and restaurants.
  • Chester Village - a picturesque neighborhood with a variety of historic homes.
  • Okemo Valley - a scenic area with plenty of outdoor activities.

Where is Chester, VT?

Chester, VT is located in the center of Vermont, right in the heart of the Green Mountains. It is a small town with a population of around 2,000 people, and is about a 30 minute drive from both Brattleboro and Rutland.

What are the most popular vacation rental amenities in Chester, VT?

The most popular vacation rental amenities in Chester, VT include:

  • Outdoor spaces such as a deck, patio, or balcony
  • Fully-equipped kitchens
  • Laundry facilities
  • High-speed internet access
  • Fireplaces

What are the top things to do in Chester, VT?

Chester, VT is a great destination for outdoor enthusiasts. Here are some of the top activities to enjoy:

  • Hiking the Green Mountains
  • Exploring the trails of the Green Mountain National Forest
  • Enjoying the scenery of the Okemo Valley
  • Touring the historic sites of Chester, VT

Whether you're looking for a day of hiking, to explore the area's history, or to simply take in the beautiful views, Chester, VT has something for everyone.

What do I need to know before visiting Chester, VT?

Before visiting Chester, VT, it's important to know a few things. You should be aware of the local weather conditions, how to get around, and what amenities are available.

  • Check the average temperatures and weather patterns for the time of year you'll be visiting.
  • Familiarize yourself with the transportation options available, like car rental, public transportation, biking, and walking.
  • Research what restaurants, shops, and entertainment venues are nearby.

What is the price range for rentals in Chester?

Vacation rentals in Chester have a price range between R 1,341-R 18,911. The average price for rentals in Chester is R 307 per night.

Explore near Chester

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration