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Chester Rentals

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Price range

Per night

$10 - $500

Chester Rentals

About Chester

183 Houses

Hugging Bear Inn - Tower Room

Chester b and b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$119

1 / 10

Amare Guesthouse, renovated in-town victorian

Chester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$230

1 / 22

Hugging Bear Inn - Bear Cub Room

Chester b and b

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$139

1 / 10

Hugging Bear Inn - Bear's Den Room

Chester b and b

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$139

1 / 11

Hugging Bear Inn & Shoppe- rent entire Inn

Chester b and b

6 bedrooms / 7 bathrooms / sleeps 18

Price per night from

$590

1 / 30

Historic 1868 Carriage House at Chester Depot

Chester guest house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$150

1 / 19

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

Chester house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$176

1 / 10

Chester House Just 12 Mins to Magic Mtn Ski Area!

Chester house

5 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 8 minutes

Price per night from

$135

1 / 24

Great rentals within 20 miles that match your search

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. Co

Responds fast! avg. 3 hours 9 minutes

Price per night from

$225

1 / 18

VERMONT cabin-- a country get-away, for fun & romance

Belmont house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 39 minutes

Price per night from

$98

1 / 20

Seasonal Rental Cozy 2 BR Apt 5 min drive to Okemo & 25 min drive to Killington

Ludlow apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$100

1 / 10

Ludlow Cabin Near Okemo Ski Lodge

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$250

1 / 27

Little Brook House at Echo Lake

Ludlow house

5 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$190

1 / 20

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

$1,295

1 / 11

3 Season Cabin - sleeping porch lake trails playground

Mount Holly log cabin

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$90

1 / 21

Beautiful Vacation Home at Strattonwald at Stratton Mountain

Stratton Mountain house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 35 minutes

Price per night from

$450

1 / 18

Charming and cozy Log cabin near Stratton Vermont

Jamaica house

4 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 18 minutes

Price per night from

$300

1 / 12

6 BR Ski Chalet in VT Green Mountains

Ludlow chalet

6 bedrooms / 2 bathrooms / sleeps 16

Price per night from

$245

1 / 39

South Face Village

Ludlow condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$300

1 / 16

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$252

1 / 8

Charming Vt. Farmhouse with spectacular mt. views. Children welcome

Londonderry house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Vacation Home” We stayed at the Humphrey's Farmhouse in august and had a great time. The home is very charming, clean and has just about every ammenity you could ask for. The house is at the top of a hill and the views are incredible, espe

Price per night from

$133

1 / 22

Gorgeous Estate with Swimming Pool Overlooking the Mountains

Newfane house

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$604

1 / 36

Mountain, Ski, & Serenity Vacation Home. 3.5 hrs from NYC and No. Jersey

Andover house

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 56 minutes

Price per night from

$101

1 / 4

Lake Warren-Alstead-Walpole-Keene- Spring Summer

Alstead cottage

4 bedrooms / 1 bathroom / sleeps 5

“Unplug , unwind and relax” Cute , clean and refreshingly quiet. My wife and I thoroughly enjoyed our week on the lake (the dogs did as well). The nearby hiking, kayaking, and local produce were great! Thanks for the memories Lake Warren!!

Price per night from

$175

1 / 20

Oma"s Kottage

Ludlow house

6 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 1 hour 52 minutes

Price per night from

$150

1 / 17

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$700

1 / 39

3 bedroom lake home on Crescent lake

Newport house

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$215

1 / 11

2016-17 Booking now for entire Ski Season $8000.00

Londonderry chalet

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 42 minutes

Price per night from

$350

1 / 16

Plymouth Home w/ Jacuzzi Near Okemo & Killington!

Plymouth house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 8 minutes

Price per night from

$340

1 / 24

Vermont home located in the mountains between Mt. Snow & Stratton Mt

Wardsboro log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$302

1 / 18

Cabin in the Big Woods - sleeping porch lake trails playground

Mount Holly log cabin

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$81

1 / 20

Light Filled Mountain Retreat Near Killington and Okemo - sleeps 6

Plymouth house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$220

1 / 16

3 BR/Bth Townhouse/Condo Grt loc. Stratton Mtn. VT

Stratton Mountain apartment

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$233

1 / 16

Weddings Retreats Discovery & Wellness! - The Blue Door Farm Resort

Landgrove house

8 bedrooms / 10 bathrooms / sleeps 22

Responds fast! avg. 43 minutes

Price per night from

$399

1 / 69

Large, Lovely, Affordable Mountain Home

Windham house

5 bedrooms / 3 bathrooms / sleeps 10

“I rented a house for a weekend and received much more than a pla” I rented the Windham County House for a weekend to hold a retreat for first year students at Middlebury College who are still adjusting to college life. This house provided us with an

Price per night from

$83

1 / 20

The Antler House

Plymouth house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 3 hours 36 minutes

Price per night from

$539

1 / 24

Beautiful Okemo chalet with Hot Tub

Ludlow chalet

4 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$325

1 / 26

Stratton 4 Bedroom Home

Stratton Mountain house

4 bedrooms / 3 bathrooms / sleeps 11

Responds fast! avg. 2 hours 22 minutes

Price per night from

$350

1 / 10
Viewing 38 of 183

About Chester

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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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