Estia Villas - Vacation Rentals in Chester
House
9.8
(
51 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
3000 ft²
-
Parking -
Balcony/Terrace -
Kitchen -
Air Conditioner
US $430
/Night
7 Nights - $3,007
Bed & Breakfast
9.7
(
73 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
247.57 ft²
-
Parking
-
Balcony/Terrace
-
View -
Air Conditioner
US $160
/Night
7 Nights - $1,120
Bed & Breakfast
9.2
(
120 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Balcony/Terrace
-
Kitchen
US $281
/Night
7 Nights - $1,968
Cabin
10.0
(
27 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $550
/Night
7 Nights - $3,850
Ski Chalet
10.0
(
11 Reviews
)
4 Bedrooms
1 Bathroom
8 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $430
/Night
7 Nights - $3,011
Ski Chalet
10.0
(
8 Reviews
)
5 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $569
/Night
7 Nights - $3,985
Cabin
10.0
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
275 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $280
/Night
7 Nights - $1,958
House
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1551 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $482
/Night
7 Nights - $3,374
See More Chester Vacation Rentals
Luxury Places to Stay in Chester
Over 89+
Luxury Places to Stay in or Near Chester
House
3 Bedrooms
2 Bathrooms
10 Guests
2400.35 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $925
/Night
7 Nights - $6,475
Cabin
10.0
(
18 Reviews
)
4 Bedrooms
2 Bathrooms
6 Guests
2316 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $768
/Night
7 Nights - $5,374
House
4 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $719
/Night
7 Nights - $5,034
House
9.6
(
4 Reviews
)
5 Bedrooms
2 Bathrooms
8 Guests
2152 ft²
-
Air Conditioner
-
Internet
-
Child Friendly -
Laundry
US $624
/Night
7 Nights - $4,371
House
5 Bedrooms
4 Bathrooms
8 Guests
4500 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $570
/Night
7 Nights - $3,988
House
9.8
(
12 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Child Friendly
US $556
/Night
7 Nights - $3,894
House
10.0
(
10 Reviews
)
5 Bedrooms
6 Bathrooms
12 Guests
5000 ft²
-
Parking
-
Spa -
Balcony/Terrace
-
Kitchen
US $537
/Night
7 Nights - $3,758
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Kitchen
-
Internet
-
Child Friendly
-
Laundry
US $499
/Night
7 Nights - $3,493
See More Chester Luxury Vacation Rentals
Find More Chester Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chester
Over 6+
Top-Rated Vacation Rentals with a Pool in or Near Chester
Cabin
9.8
(
73 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
650 ft²
-
Parking
-
Pool -
Balcony/Terrace
-
Kitchen
US $344
/Night
7 Nights - $2,411
House
9.8
(
16 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $340
/Night
7 Nights - $2,378
House
9.4
(
39 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $209
/Night
7 Nights - $1,462
Other
9.2
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $523
/Night
7 Nights - $3,662
Other
8.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $189
/Night
7 Nights - $1,323
Other
5.0
(
1 Review
)
5 Bedrooms
2 Bathrooms
10 Guests
-
Pool
-
Kitchen
-
Air Conditioner
-
Child Friendly
US $258
/Night
7 Nights - $1,806
See More Chester Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Chester
Over 29+
Pet-Friendly Vacation Rentals in or Near Chester
Cabin
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
275 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $280
/Night
7 Nights - $1,958
House
9.7
(
3 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
742.71 ft²
-
Parking
-
Internet
-
Pet Friendly -
Child Friendly
US $242
/Night
7 Nights - $1,694
Cabin
9.8
(
25 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
500 ft²
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $161
/Night
7 Nights - $1,130
House
9.8
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
738 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $286
/Night
7 Nights - $2,003
House
9.4
(
22 Reviews
)
4 Bedrooms
1 Bathroom
8 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $409
/Night
7 Nights - $2,862
New
Cabin
1 Bedroom
1 Bathroom
2 Guests
-
Spa
-
Kitchen
-
Air Conditioner
-
Internet
US $305
/Night
7 Nights - $2,134
New
Cabin
1 Bedroom
1 Bathroom
2 Guests
-
Spa
-
Kitchen
-
Air Conditioner
-
Internet
US $305
/Night
7 Nights - $2,134
House
10.0
(
244 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $184
/Night
7 Nights - $1,291
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io
Large Vacation Homes & Villas in Chester
Over 10+
Large Vacation Homes & Villas in or Near Chester
House
10.0
(
41 Reviews
)
5 Bedrooms
3 Bathrooms
9 Guests
2700 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $343
/Night
7 Nights - $2,399
Bed & Breakfast
8.9
(
74 Reviews
)
7 Bedrooms
7 Bathrooms
16 Guests
-
Parking
-
Skiing -
Balcony/Terrace
-
View
US $232
/Night
7 Nights - $1,622
Cabin
10.0
(
3 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Kitchen
-
Internet
-
Pet Friendly
US $329
/Night
7 Nights - $2,300
House
9.8
(
8 Reviews
)
5 Bedrooms
3 Bathrooms
13 Guests
2564 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $583
/Night
7 Nights - $4,080
House
5.0
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
11 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Pet Friendly
US $425
/Night
7 Nights - $2,975
House
8 Bedrooms
4 Bathrooms
16 Guests
4110 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $811
/Night
7 Nights - $5,676
House
10.0
(
3 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
5000 ft²
-
Hot Tub
-
Parking
-
Spa
-
Balcony/Terrace
US $830
/Night
7 Nights - $5,810
House
10.0
(
1 Review
)
6 Bedrooms
4 Bathrooms
12 Guests
3000 ft²
-
Parking
-
Ocean View -
Balcony/Terrace
-
View
US $1,074
/Night
7 Nights - $7,518
See More Family Vacation Rentals in Chester on FVR
Wheelchair Accessible Vacation Homes in Chester
Over 1+
Wheelchair Accessible Vacation Homes in or Near Chester
House
4.9
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2000 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $269
/Night
7 Nights - $1,883
Chester Vacation Rentals and Airbnb Places to Stay Under $200
Over 9+
Chester Vacation Rentals and Airbnb Places to Stay Under $200
Bed & Breakfast
9.2
(
21 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
150 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $193
/Night
7 Nights - $1,348
US $200
/Night
7 Nights - $1,400
US $173
/Night
7 Nights - $1,213
House
9.0
(
14 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
200 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $190
/Night
7 Nights - $1,333
Bed & Breakfast
7.8
(
124 Reviews
)
1 Bedroom
1 Bathroom
-
Kitchen
-
Bedding/Linens
US $140
/Night
7 Nights - $982
House
3.5
(
10 Reviews
)
4 Bedrooms
2 Bathrooms
7 Guests
1600 ft²
-
Kitchen
-
Child Friendly
-
TV
US $169
/Night
7 Nights - $1,183
House
2 Bedrooms
2 Bathrooms
6 Guests
1176 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $185
/Night
7 Nights - $1,298
House
3 Bedrooms
1 Bathroom
5 Guests
-
Internet
-
Child Friendly
-
Laundry
-
Bedding/Linens
US $173
/Night
7 Nights - $1,211
See More Chester Vacation Rental Deals
Instantly Bookable Vacation Homes in Chester
Over 23+
Instantly Bookable Vacation Homes in or Near Chester
House
9.8
(
18 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $335
/Night
7 Nights - $2,344
Ski Chalet
9.4
(
6 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $375
/Night
7 Nights - $2,628
New
Apartment
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $259
/Night
7 Nights - $1,815
House
10.0
(
39 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
4300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $325
/Night
7 Nights - $2,274
Cabin
10.0
(
10 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
300 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $252
/Night
7 Nights - $1,763
House
10.0
(
5 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $338
/Night
7 Nights - $2,366
House
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
2200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $576
/Night
7 Nights - $4,034
House
10.0
(
2 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
2300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $564
/Night
7 Nights - $3,949
See More Chester Short-Term Vacation Rentals
About Chester Vacation Rentals
With more than 98 Chester vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Chester, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chester. Places to stay near Chester are 1043.43 ft² on average, with prices averaging US $381 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Chester with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chester
| Type | Count |
|---|---|
| Vacation Homes | 61 |
| Cabin Rentals | 11 |
| B&B | 9 |
| Holiday Apartments | 6 |
| Others | 4 |
| Ski Chalet Rentals | 4 |
| Hotels | 3 |
Use these Quick Filters to Find a Vacation Rental in Chester
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chester.
Weather in Chester
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
Top Attractions Around Chester, VT
Estiavillas offers a large selection of top attractions around Chester. Research things to do on your vacation before you visit Chester.
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
Other Places to Stay Near Chester, VT
Chester Vacation Rental Frequently Asked Questions
Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
How many vacation rentals are available in Chester?
Currently, the total number of properties listed in 2026 is over 98 in the Chester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester.
