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Chester Rentals

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102 Houses

Amare Guesthouse, renovated in-town victorian

Chester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$273

Hugging Bear Inn RENT ENTIRE INN

Chester b&b

6 bedrooms / 7 bathrooms / sleeps 18

Price per night from

$1,161

Historic Chester House 10-30 Mins to 5 Mountains!

Chester house

5 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 7 minutes

Price per night from

$166

The 1843 Stone House - Chester, VT (3bdrm/ 2 ba)

Chester house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$233

Great rentals within 20 miles that match your search

Elegant victorian with free wifi, private washer/dryer - Near Okemo

Proctorsville house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 1 minutes

Price per night from

$464

Cozy Historic Hilltop Cottage

Brownsville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$172

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

15 bedrooms / 12 bathrooms / sleeps 44

Price per night from

$2,903

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Ludlow townhouse

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$474

Heyer House

Wardsboro house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$178

Slopeside Townhome in Bromley Village

Peru townhouse

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$326

Stratton Ten Pines - Spectacular Timberframe Home

Jamaica house

6 bedrooms / 4 bathrooms / sleeps 16

Responds fast! avg. 1 hour 48 minutes

Price per night from

$1,781

South Face Village

Ludlow condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$653

Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo

Proctorsville house

8 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$475

Kassmel's Mountain Haus

West Wardsboro house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$357

5 STAR HOME - HOT TUB SAUNA BUS TO STRATTON LIFTS

Bondville house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$593

Clean, Affordable, 2 BR Apt 5 min drive to Okemo & 25 min drive to Killington Mt

Ludlow apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$89

Newly Remodeled Townhome

Jamaica townhouse

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$594

Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

Peru townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$351

Whispers of the North

West Wardsboro house

6 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$262

Stunning Designers VT Home Luxurious, 5600 SF, 3D Home Theater, Gourmet kitchen

Bondville villa

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$594

Luxury Lakefront Home near Okemo

Ludlow house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$766

Bromley Farm Ski House

Peru house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$653

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$588

Ski Southern VT! Perfect home for large groups ... HOT TUB!

Londonderry house

5 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$653

Live & Breathe VT- Village Home, Yoga Studio, Ski!

Jamaica house

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$297

Okemo VT Mansion - Sleep 17 Chef Optional

Cavendish manor house

6 bedrooms / 10 bathrooms / sleeps 17

Price per night from

$1,365

2016-17 Booking now for entire Ski Season $8000.00

Londonderry chalet

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$416

Ski-in/out Luxury 3 Bedroom & 3 Bathroom Okemo Penthouse Condo at Jackson Gore

Ludlow apartment

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,537

**Spectacular Green Mtn Natl Forest Retreat **

Manchester log cabin

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$594

4 Minutes to Okemo Mountain

Proctorsville house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$523

Charming and cozy Log cabin near Stratton Vermont

Jamaica house

4 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$356

Incredible Home Sets Bar for Stratton Views&Luxury

Stratton Mountain house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 4 minutes

Price per night from

$950

Ludlow Cabin Near Okemo Ski Lodge

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$297

Charming Ski Chalet Close to Main St & Okemo Mtn

Ludlow chalet

3 bedrooms / 2 bathrooms / sleeps 13

Price per night from

$327

Live the real Vermont Experiance

Grafton house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$119

Spotless newer ski home

Cavendish house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$534

A Vermont House for All Seasons

Ludlow cottage

3 bedrooms / 2 bathrooms / sleeps 6

“Perfect, just PERFECT” This house is just perfect for my group of 6. Everything is exactly as described. It's clean, warm & cozy, has everything that you need. Owner is very nice & thoughtful as well, you can find little notes throughout the house. Could not have asked for more!

Responds fast! avg. 1 hour 27 minutes

Price per night from

$267

Stratton 4 Bedroom Home

Stratton Mountain house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 3 hours 8 minutes

Price per night from

$416

Viewing 38 of 102
rentals in Chester

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About Chester

For scenic beauty in the middle of a vibrant and historic area, consider Chester for your next vacation destination! Most of the shops and restaurants throughout Chester can be found along Main Street, but the town is small enough that anything you wish to reach can be accessed by foot.

While you're in Chester, be sure to also make time for these destinations that highlight the rich history and beautiful scenery of the area:

  • Chester Historical Society: Learn more about the town's proud history with the exhibits and artifacts found at this long-standing museum.
  • Chester Vietnam Conflict Monument: Located in the middle of downtown, this monument is dedicated to the men and women in Chester who served in the Vietnam War.
  • Play Golf: Tater Hill Golf Club is a nine-hole course that provides an afternoon of fun for all ages and skill levels.
  • Go Skiing: Nearby Okemo Mountain is considered one of the premier destinations for skiing in the entire country.

There are great events in Chester throughout the year, ranging from live performance to parties that stretch across town. Watch chainsaw carvers show off their skills at the Big Buzz Chainsaw Carving Festival in October, sample the works of over 60 local craftsmen and artisans at Chester's Fall Craft Fair in September, or watch dozens of hot air balloons soar through the sky at the Quechee Vermont Balloon Festival in May.

Whether you're looking for a picturesque condo or apartment just steps from the outdoor recreational options throughout town, or a cozy cabin with mountain views, there's a vacation rental that will put you exactly where you want to be in Chester.

If you're looking to explore the rest of Vermont, Chester is a great location to use as a base for a series of day trips. The big city of Burlington and the outdoor attractions of Stowe can both be reached within an hour by car.

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