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Chester Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
41 rentals in Chester.
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!, holiday rental in Chester
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!, holiday rental in Chester
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!, holiday rental in Chester

Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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King & Queen Suite in Historic Inn Circa 1780, holiday rental in Chester
King & Queen Suite in Historic Inn Circa 1780, holiday rental in Chester
King & Queen Suite in Historic Inn Circa 1780, holiday rental in Chester

King & Queen Suite in Historic Inn Circa 1780

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Riverfront, family fun, amazing rec room, close to Magic & Okemo, holiday rental in Chester
Riverfront, family fun, amazing rec room, close to Magic & Okemo, holiday rental in Chester
Riverfront, family fun, amazing rec room, close to Magic & Okemo, holiday rental in Chester

Riverfront, family fun, amazing rec room, close to Magic & Okemo

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Whimsical Room & Private Bathroom in Historic Inn, holiday rental in Chester
Whimsical Room & Private Bathroom in Historic Inn, holiday rental in Chester
Whimsical Room & Private Bathroom in Historic Inn, holiday rental in Chester

Whimsical Room & Private Bathroom in Historic Inn

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Log Cabin -  Cozy, Quaint & Scenic and Ready for Your Enjoyment!, holiday rental in Chester
Log Cabin -  Cozy, Quaint & Scenic and Ready for Your Enjoyment!, holiday rental in Chester
Log Cabin -  Cozy, Quaint & Scenic and Ready for Your Enjoyment!, holiday rental in Chester

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Zen of the Woods Tiny Cabin in Okemo Valley, holiday rental in Chester
Zen of the Woods Tiny Cabin in Okemo Valley, holiday rental in Chester
Zen of the Woods Tiny Cabin in Okemo Valley, holiday rental in Chester

Zen of the Woods Tiny Cabin in Okemo Valley

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Room in Historic Inn! 20 Minutes to Okemo!, holiday rental in Chester
Room in Historic Inn! 20 Minutes to Okemo!, holiday rental in Chester
Room in Historic Inn! 20 Minutes to Okemo!, holiday rental in Chester

Room in Historic Inn! 20 Minutes to Okemo!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Honeymoon Suite with Jacuzzi Tub in Historic Inn, holiday rental in Chester
Honeymoon Suite with Jacuzzi Tub in Historic Inn, holiday rental in Chester
Honeymoon Suite with Jacuzzi Tub in Historic Inn, holiday rental in Chester

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., holiday rental in Chester
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., holiday rental in Chester
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., holiday rental in Chester

This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., holiday rental in Chester
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., holiday rental in Chester
This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT., holiday rental in Chester

This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vermont Hillside Cottage w/Great View - Pet Friendly, holiday rental in Chester
Vermont Hillside Cottage w/Great View - Pet Friendly, holiday rental in Chester
Vermont Hillside Cottage w/Great View - Pet Friendly, holiday rental in Chester

Vermont Hillside Cottage w/Great View - Pet Friendly

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquility awaits for your stay at our cherished log home on 6 secluded acres., holiday rental in Chester
Tranquility awaits for your stay at our cherished log home on 6 secluded acres., holiday rental in Chester
Tranquility awaits for your stay at our cherished log home on 6 secluded acres., holiday rental in Chester

Tranquility awaits for your stay at our cherished log home on 6 secluded acres.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!, holiday rental in Chester
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!, holiday rental in Chester
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!, holiday rental in Chester

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Historic Home in Vermont, holiday rental in Chester
Charming Historic Home in Vermont, holiday rental in Chester
Charming Historic Home in Vermont, holiday rental in Chester

Charming Historic Home in Vermont

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, holiday rental in Chester
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, holiday rental in Chester
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby, holiday rental in Chester

Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort, holiday rental in Chester
Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort, holiday rental in Chester
Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort, holiday rental in Chester

Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cheerful residential home with lots of space, holiday rental in Chester
Cheerful residential home with lots of space, holiday rental in Chester
Cheerful residential home with lots of space, holiday rental in Chester

Cheerful residential home with lots of space

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy 4bd - Ski Okemo, Killington, Magic & Bromley, holiday rental in Chester
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley, holiday rental in Chester
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley, holiday rental in Chester

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!, holiday rental in Chester
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!, holiday rental in Chester
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!, holiday rental in Chester

UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Vermont Farmhouse, perfect for summer and fall foliage getaways!, holiday rental in Chester
Amazing Vermont Farmhouse, perfect for summer and fall foliage getaways!, holiday rental in Chester
Amazing Vermont Farmhouse, perfect for summer and fall foliage getaways!, holiday rental in Chester

Amazing Vermont Farmhouse, perfect for summer and fall foliage getaways!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres, holiday rental in Chester
15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres, holiday rental in Chester
15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres, holiday rental in Chester

15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR, holiday rental in Chester
Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR, holiday rental in Chester
Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR, holiday rental in Chester

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Circa 1868 Chester Home-Less than 20 MIN TO OKEMO, holiday rental in Chester
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO, holiday rental in Chester
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO, holiday rental in Chester

Circa 1868 Chester Home-Less than 20 MIN TO OKEMO

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Work, Ski, Relax - Big Restored 1860s Farmhouse, holiday rental in Chester
Work, Ski, Relax - Big Restored 1860s Farmhouse, holiday rental in Chester
Work, Ski, Relax - Big Restored 1860s Farmhouse, holiday rental in Chester

Work, Ski, Relax - Big Restored 1860s Farmhouse

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spacious retreat with private hot tub, game room, deck, fireplace, & W/D, holiday rental in Chester
Spacious retreat with private hot tub, game room, deck, fireplace, & W/D, holiday rental in Chester
Spacious retreat with private hot tub, game room, deck, fireplace, & W/D, holiday rental in Chester

Spacious retreat with private hot tub, game room, deck, fireplace, & W/D

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!, holiday rental in Chester
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!, holiday rental in Chester
Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!, holiday rental in Chester

Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 5-bedroom chalet with AC and WiFi in charming Chester, holiday rental in Chester
Spacious 5-bedroom chalet with AC and WiFi in charming Chester, holiday rental in Chester
Spacious 5-bedroom chalet with AC and WiFi in charming Chester, holiday rental in Chester

Spacious 5-bedroom chalet with AC and WiFi in charming Chester

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!, holiday rental in Chester
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!, holiday rental in Chester
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!, holiday rental in Chester

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!, holiday rental in Chester
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!, holiday rental in Chester
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!, holiday rental in Chester

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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FOUR SEASON HOME NEAR OKEMO, holiday rental in Chester
FOUR SEASON HOME NEAR OKEMO, holiday rental in Chester
FOUR SEASON HOME NEAR OKEMO, holiday rental in Chester

FOUR SEASON HOME NEAR OKEMO

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Thistle House at Camp Greenwood Vermont with Sauna, holiday rental in Chester
Thistle House at Camp Greenwood Vermont with Sauna, holiday rental in Chester
Thistle House at Camp Greenwood Vermont with Sauna, holiday rental in Chester

Thistle House at Camp Greenwood Vermont with Sauna

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sage House at Camp Greenwood Vermont with Sauna, holiday rental in Chester
Sage House at Camp Greenwood Vermont with Sauna, holiday rental in Chester
Sage House at Camp Greenwood Vermont with Sauna, holiday rental in Chester

Sage House at Camp Greenwood Vermont with Sauna

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck, holiday rental in Chester
Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck, holiday rental in Chester
Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck, holiday rental in Chester

Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches., holiday rental in Chester
Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches., holiday rental in Chester
Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches., holiday rental in Chester

Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Cairn,  1840s Cozy Stone Cottage, Pet Friendly, holiday rental in Chester
The Cairn,  1840s Cozy Stone Cottage, Pet Friendly, holiday rental in Chester
The Cairn,  1840s Cozy Stone Cottage, Pet Friendly, holiday rental in Chester

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Chester Farmhouse – peaceful and close to everything!, holiday rental in Chester
Charming Chester Farmhouse – peaceful and close to everything!, holiday rental in Chester
Charming Chester Farmhouse – peaceful and close to everything!, holiday rental in Chester

Charming Chester Farmhouse – peaceful and close to everything!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy farmhouse w/ TV, wifi, w/d, dvd player, kitchen, board games, holiday rental in Chester
Cozy farmhouse w/ TV, wifi, w/d, dvd player, kitchen, board games, holiday rental in Chester
Cozy farmhouse w/ TV, wifi, w/d, dvd player, kitchen, board games, holiday rental in Chester

Cozy farmhouse w/ TV, wifi, w/d, dvd player, kitchen, board games

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3-bedrooms and bath in welcoming Chester with WiFi, AC., holiday rental in Chester
3-bedrooms and bath in welcoming Chester with WiFi, AC., holiday rental in Chester
3-bedrooms and bath in welcoming Chester with WiFi, AC., holiday rental in Chester

3-bedrooms and bath in welcoming Chester with WiFi, AC.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Renovated ski house near Okemo and Stratton, holiday rental in Chester
Renovated ski house near Okemo and Stratton, holiday rental in Chester
Renovated ski house near Okemo and Stratton, holiday rental in Chester

Renovated ski house near Okemo and Stratton

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Rustic 150-year-old farmhouse, Jacuzzi included, holiday rental in Chester
Rustic 150-year-old farmhouse, Jacuzzi included, holiday rental in Chester
Rustic 150-year-old farmhouse, Jacuzzi included, holiday rental in Chester

Rustic 150-year-old farmhouse, Jacuzzi included

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Custom Home on 40+ Acres, holiday rental in Chester
Amazing Custom Home on 40+ Acres, holiday rental in Chester
Amazing Custom Home on 40+ Acres, holiday rental in Chester

Amazing Custom Home on 40+ Acres

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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Showing results 1-41 of 41
Frequently Asked Questions about Chester