Chester Rentals

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Hugging Bear Inn RENT ENTIRE INN

Chester b&b

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 18

Price per night from

$1,234

Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse

Chester house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,030

Great rentals within 20 miles that match your search

2 Bedroom/2 Bath Condo

Stratton Mountain apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$343

Whispers of the North

West Wardsboro house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$253

6 BR Ski Chalet with Boats in VT Green Mountains

Ludlow chalet

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$373

Vermont Country Lake House

Ludlow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$287

Price per night from

$402

Vermont Log Home On 21 Acres Btwn Okemo/killington

Mount Holly house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$431

Cozy Historic Hilltop Cottage

Brownsville house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$213

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

$459

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 58 minutes

Price per night from

$104

South Face Village

Ludlow condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$631

Oma"s Kottage

Ludlow house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$345

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Reading house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$287

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

Peru townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 2 minutes

Price per night from

$339

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$402

A Family Place

Bondville house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$413

Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Proctorsville house

  • 8 bedrooms
  • 4 bathrooms
  • sleeps 16

Price per night from

$459

Price per night from

$1,125

Chase House Inn - Edwin Stanton Room

Cornish house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

1820 House

Perkinsville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$345

BEAUTIFUL STRATTON! 5 BEDS-5 BATHS HOME w/VIEWS, ON SHUTTLE

Stratton Mountain house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$2,237

A Quiet Retreat in Rural New Hampshire

Cornish house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$362

3 Season Cabin - sleeping porch lake trails

Mount Holly log cabin

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Responds fast! avg. 1 hour 58 minutes

Price per night from

$104

Cute VT Bungalow With 180 Degree View of NH

Springfield apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$230

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ shared pool and hot tub

Bondville condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

Price per night from

$171

Beautiful Country Luxury Waterfront Lake Home

Unity cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

Price per night from

$980

Price per night from

$1,374

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$802

Vermont Cottage Lake Amherst

Plymouth cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$802

Contemporary Ski Chalet Minutes to Hiking Dining Parks

South Londonderry house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$1,444

Price per night from

$285

Okemo Mountain Lodge A-108 Ski In/Ski Out

Ludlow condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$229

25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails

Ludlow apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$401

“The Perfect Vermont Getaway” When I visit Vermont in winter, I tend to go with a mixed crowd. Part of our group are avid skiers/snowboarders, the other part (well, me) are not. This house allows you to experience the best of both worlds, with something for everyone. Situated on top of the mountain (within walking distance to the lodge and with a shuttle that can pick you up right outside the front door), it's in the absolute perfect location for those who like to lace up their boots and hit the slopes. For anyone not playing snow bunny for the day, you are smack dab in the middle of Okemo with plenty of cafes, shopping, and scenic walks just down the hillside (or a very short drive away if you wish to explore). The house itself is also a fantastic, light, open space that is comfortable no matter which straw you draw for beds (we got the twins in the upstairs loft and had one of the soundest sleeps I'd had all winter). Plus, who doesn't love a hot tub. You never feel cramped even with a full house. The living room is an amazing space to just sip coffee and read your book in the morning sunshine or in front of the fire. The owners are extremely knowledgeable, responsive, and helpful, and made sure our stay was top-notch. They have everything outlined for you in a book when you arrive and are there for you should you have any questions. I can't wait to go back next winter!

Price per night from

$1,832

Walk to ski trials on Okemo! Private Luxury Chalet

Ludlow chalet

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$1,368

Multi Level Stratton Mountain Retreat

Bondville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Price per night from

$1,145

The Grafton Lodge

Grafton lodge

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 20

Price per night from

$2,175

Viewing 38 of 44
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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