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Vacation rentals in Chester, Vermont, United States

Spacious living room

Fully stocked kithcen

Queen bedroom with natural light

Welcome to our cozy home!

Rural Chester Farmhouse

3 bedrooms·2 baths

Chester • Vermont

Valley Views with Hot Tub

Valley Views with Hot Tub

Valley Views with Hot Tub

Valley Views with Hot Tub

Valley Views with Hot Tub

Valley Views with Hot Tub

4 bedrooms·3½ baths

Windham • Vermont

Magic Circle home-Private Hot Tub, Fire pit+ more!

Magic Circle home-Private Hot Tub, Fire pit+ more!

Magic Circle home-Private Hot Tub, Fire pit+ more!

Magic Circle home-Private Hot Tub, Fire pit+ more!

Magic Circle home-Private Hot Tub, Fire pit+ more!

Magic Circle home-Private Hot Tub, Fire pit+ more!

4 bedrooms·2 baths

Londonderry • Vermont

Welcome to our chalet!

We have 2 pellet stoves!

Comfort is our priority!

Hot Tub Chalet on Magic Mountain

5 bedrooms·2½ baths

Londonderry • Vermont

Enjoy a movie and some theater style popcorn in our living room and open kitchen

Jacuzzi Hot Tub

The kitchen is stocked with everything you need to wow your family and friends with your culinary abilities, or just keep the drinks cold and go out, all Weston has to offer is mere footsteps

Challenge each other to a game of basketball, arcade classic Mortal Kombat 3 or one of many others - while the rest of the crew catches a flick waiting for their turn to play.

Feel the warmth of 200 year old post and beam construction

The Historic Rideout

6 bedrooms·6 baths

Weston • Vermont

4.92(36 reviews)

1 640,34 $ USD 1 531,89 $ USD total pour 3 nuits

2–5 nov. 2026

Londonderry Loft with Sauna

Londonderry Loft with Sauna

Londonderry Loft with Sauna

Londonderry Loft with Sauna

Londonderry Loft with Sauna

Londonderry Loft with Sauna

4 bedrooms·2 baths

Londonderry • Vermont

Relax by the fire in our 8 leather recliners & 3 bean bag chairs

Eat Breakfast by the Pellet Stove & Feel the vibes of 1830s Post & Beam Construction

Our Expansive Chef's Kitchen

Have yourself a steam in our Sauna

Red Brick Retreat

8 bedrooms·6 baths

Londonderry • Vermont

5(25 reviews)

$618 – $2 060/ nuit(hors frais et taxes)

Open concept for larger groups

Seasonal Fire Pit with Grill in our yard (not open during winter)

Family room with giant 65" Smart VT

Tic Tac Toe anyone?

Seating area for meals

Trailside Chalet

5 bedrooms·2½ baths

Washington County • Vermont

4.93(87 reviews)

1 097,47 $ USD 934,75 $ USD total pour 3 nuits

1–4 nov. 2026

Winter Wonderland! Great Okemo rental.

Lazy Afternoon in Paradise

Open Space & Relaxation. The Ultimate Social Distancing Escape!

Fresh Air with Wifi. (If You're into that Sort of Thing....)

Classic Vermont - Historic Renovated Dairy Farm (No Cows Anymore)

2 Bdrm, Lower Level, Okemo, 25 Acre Mtn Playground

2 bedrooms·1 bath

Cavendish • Vermont

5(27 reviews)

1 374,89 $ USD total pour 5 nuits

31 oct. – 5 nov. 2026

Front View of The Farmhouse - The Second Story is All Yours

Open Space & Relaxation. The Ultimate Social Distancing Escape!

Classic Vermont - Historic Renovated Dairy Farm (No Cows Anymore)

Lazy Afternoon in Paradise

Fresh Air with Wifi. (If You're into that Sort of Thing....)

2 Bdrm, Upper Level, Okemo, 25 Acre Mtn Playground

2 bedrooms·1 bath

Cavendish • Vermont

5(13 reviews)

1 374,89 $ USD total pour 5 nuits

31 oct. – 5 nov. 2026

Winter Wonderland

Hot tub and Sauna.. and silence

Try 30 minutes in the sauna...after full day of skiing

Living Room Retreat: Sunlit space with vaulted ceilings and stylish decor for perfect relaxation!

Delight in the hottub when its cool outside

Stratton Ski Haus

4 bedrooms·2½ baths

Jamaica • Vermont

2 017,80 $ USD 1 571,41 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026

Glen Rd Mountain Retreat

3 bedrooms·2 baths

Peru • Vermont

1 259,66 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026

Property grounds

Summer fun on lake - great for 2 families or 3 couples - newly remodeled

4 bedrooms·2 baths

Windsor County • Vermont

4 000,00 $ USD total pour 5 nuits

31 oct. – 5 nov. 2026

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 bedrooms·2 baths

Ludlow • Vermont

5(107 reviews)

$550 – $650/ nuit(hors frais et taxes)

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

Drop Point Cabin

4 bedrooms·3 baths

Jamaica • Vermont

4.72(25 reviews)

Private Cabin Retreat | near Stratton & Mt. Snow

Private Cabin Retreat | near Stratton & Mt. Snow

4 bedrooms·3 baths

Jamaica • Vermont

1 054,92 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026

Enjoy casual conversations in this cozy living room that is flooded with natural light during the day.

High speed internet available for quick connections and streaming video.

The house is a custom timber frame with distinct and timeless styling that blends into the surrounding area.

Newly added washer and dryer for quick cleanups or drying skiing gear.

Star gazing at night is a perfect way to unwind and enjoy the seclusion.

Tranquil Brookside Retreat with Hot Tub & Firepit

4 bedrooms·2½ baths

Peru • Vermont

5(1 review)

1 412,84 $ USD total pour 3 nuits

7–10 nov. 2026

Front of the house

Cubbies and boot warmers

Spacious mud room

Space for all your gear

Upstairs living room

Burnt Hill Chalet

3 bedrooms·2 baths

Winhall • Vermont

3 640,00 $ USD total pour 5 nuits

31 oct. – 5 nov. 2026

Outdoor pool is open now!

Welcome to the loft

Walk out balcony

Enough space fore the whole crew

Stratton Loft with Pool

4 bedrooms·2 baths

Winhall • Vermont

New stainless steel appliances

Sauna with Green Mountain View’s

3 bedrooms·3 baths

Jamaica • Vermont

Property grounds

Reading Farms Estate Front Lawns

Reading Farms Estate

15 bedrooms·10 baths

Reading • Vermont

12 292,00 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

Ski Lodge Hideaway: 5 minutes to Stratton mountain

4 bedrooms·4 baths

Winhall • Vermont

5(6 reviews)

1 150,79 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR image 1

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR image 2

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR image 3

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR image 4

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR image 5

NirvanaSanctuary~HotTub~FirePit~Dogs~Okemo + ~2BR

2 bedrooms·3 baths

Plymouth • Vermont

5(31 reviews)

1 593,00 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo~1BR

Aerial view of Lake Amherst

Large screened-in porch overlooking the lake.

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo~1BR

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo~1BR

1 bedroom·2 baths

Plymouth • Vermont

5(34 reviews)

1 107,00 $ USD total pour 3 nuits

31 oct. – 3 nov. 2026