1283+ Hotel & Resort Deals in Chester |
  1. USA
  2. Vermont
  3. Central Vermont- Killington
  4. Chester

Chester Hotels, Resorts, and Rentals

About Chester Vacation Rentals

There are more than 1283 places to stay in Chester that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chester.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chester, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chester. Places to stay near Chester are 1164.16 ft² on average, with prices averaging GB £419 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chester with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

Show more
Show less

Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chester

Type Count
Vacation Homes 614
Holiday Apartments 142
Cabin Rentals 75
Ski Chalet Rentals 48
Others 26
B&B 15
Cottages 15
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chester

★ Pro Tip: Hotala.uk has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Chester.

Weather in Chester, VT

View the weather forecast for Chester before booking your Chester Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Chester's Top Attractions

Hotala.uk can help you find hotels, resorts, and rentals near many of Chester's top attractions, neighborhoods, and points of interest.


DaVallia Art & Accents
Bonnie's Bundles Dolls
Stratton Mountain Resort
Killington Resort
Okemo Mountain Resort
Bromley Mountain Ski Resort
Magic Mountain Ski Resort
Jackson Gore Ski Resort at Okemo
Bellows Falls Opera House
American Express Ski Lift
Stratton Mountain Summit Gondola Ski Lift
Vermont Country Store
Weston Playhouse
Landmark College
The Putney School
Viking Nordic Center
Weston Priory
Mt Ascutney State Park
Ball Mountain Dam
Mount Ascutney

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Chester Depot 224 Properties
DaVallia Art & Accents 48 Properties
Bonnie's Bundles Dolls 48 Properties

Frequently Asked Questions About Chester?

What are the top hotels or resorts in Chester?

You have a lot of choices in or near Chester. If you need a hotel in the Chester area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chester:

How many vacation rentals have private pools in Chester?

There are 41 accommodation options with private pools in or near Chester. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Chester is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Chester, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Chester:

How many hotels, resorts, or rentals are available in Chester?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 1283 in the Chester area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chester.

Nearby Neighborhood (1) 
Neighborhood Property Count
Chester Depot Hotel & Resort Deals in Chester, Vermont 224

People Also Ask

There are 25 hotels in Chester 5 resorts, and 831 rentals

Recently Booked Hotels, Resorts, or Rentals in Chester