Location

Dates

Guests

Vacation rentals in Windsor County, Vermont, United States

Destaque

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

4 bedrooms·3 baths

Plymouth • Vermont

5(70 reviews)

2294,20 $ USD total por 3 noites

09/11/2026 – 12/11/2026

Wrap Around Deck

Killington Grandview House

7 bedrooms·6½ baths

Mendon • Vermont

4.86(7 reviews)

4576,50 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

2072,00 $ USD total por 3 noites

09/11/2026 – 12/11/2026

View of the house from the driveway. On over an acre, surrounded by trees.

View of the house as you head up the driveway. House sits on an acre+ lot.

Kitchen with space for two at the counter.

Upgraded kitchen with quartz counters and stainless steel appliances.

Dining room & kitchen combo opens to the living room too for easy conversation.

The Crooked House

3 bedrooms·2½ baths

Stockbridge • Vermont

5(100 reviews)

971,00 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

1191,00 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

1705,00 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

1104,88 $ USD total por 5 noites

09/11/2026 – 14/11/2026

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)

1104,88 $ USD total por 5 noites

09/11/2026 – 14/11/2026

Living room is equipped with large handmade Chesterfield leather sofa, two vintage leather club chairs and vintage leather recliner. An exceptionally large wood-burning fireplace flanked by antique ski equipment adds warmth for cold Vermont nights.

Living room with large handmade Chesterfield leather sofa, two vintage leather club chairs and vintage leather recliner chair is perfect for snuggling up in front of fire with a good book, or binging on a new Netflix series.

The open plan living and dining room with 8 seat table and antique handmade ski light fixture make Kilbourne Lodge a perfect place to both entertain and relax.

Present day Kilbourne Lodge. A mid-century angled roof ski chalet with large accent stone wall. Front deck features a vintage 2-seater ski lift chair painted in bright red. 100% Instagram worthy!

King bed with memory foam mattress, individual reading lights and ski-shoe side-tables.

Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer

3 bedrooms·2 baths

Killington • Vermont

4.91(33 reviews)

1158,60 $ USD total por 3 noites

09/11/2026 – 12/11/2026

1930s-era cottage.

Hot tub open to the outside and under cover.

Primary bedroom with king bed. Featuring a Puffy mattress, fine linens, plenty of pillows, and a down comforter.

View of the lake from this bedroom

Large screened-in front porch overlooking the lake. Listen to water fowl and peepers at night.

Amherst Guest Cottage ~ One Bedroom

1 bedroom·2 baths

Plymouth • Vermont

1191,00 $ USD total por 3 noites

09/11/2026 – 12/11/2026

House facade from driveway

Fully equipped kitchen with refrigerator, dishwasher, microwave and gas range

Bathroom with shower and copper sink.

Combo washer/dryer

Breakfast island separates kitchen from living area.

Custom-built Tiny House on forested lot near Quechee

1 bedroom·1 bath

Hartland • Vermont

4.87(71 reviews)

836,51 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

1097,47 $ USD 934,75 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

3930,58 $ USD 3274,27 $ USD total por 3 noites

09/11/2026 – 12/11/2026

Our farm, wedding ski rental mountain setting

Epic Farm, House, Barn image 16

Barn wedding - farm wedding booked custom Satoyama Mountain Farm

Ski house, great room with dining rooms in back

Epic Farm, House, Barn image 4

Epic Mountain Views, House, Farm Stay, Barn

7 bedrooms·3½ baths

Rochester • Vermont

4.9(29 reviews)

3160,00 $ USD 2358,10 $ USD total por 3 noites

09/11/2026 – 12/11/2026

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)

1640,34 $ USD 1423,42 $ USD total por 3 noites

09/11/2026 – 12/11/2026

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

The Ultimate Vermont Getaway

4 bedrooms·3 baths

Rutland • Vermont

5(10 reviews)

1053,76 $ USD total por 3 noites

11/11/2026 – 14/11/2026

A queen bed and queen sofa bed share the studio, with seating close by for downtime between outings.

See how the bed, sofa and television fit within the open studio before you arrive.

The sofa sits beside a coffee table, with a dresser and closet nearby for your things.

A Keurig, microwave and mini fridge sit near the entry. This studio does not have a kitchen.

The wall-mounted television faces the sleeping area for a quiet evening in.

Killington Studio 531: Queen Bed & Queen Sofa

0 bedrooms·1 bath

Killington • Vermont

4.82(57 reviews)

843,77 $ USD total por 3 noites

09/11/2026 – 12/11/2026

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

Fall in Mount Holly

Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

4 bedrooms·2 baths

Mount Holly • Vermont

5(37 reviews)

$299/ noite(excl. taxas & impostos)

Heavenly Killington 16 ppl, 7 bedrooms, 4 bathrooms, 11 beds. Free parking for 10+ cars. Tesla charger.

Heavenly Killington 16 ppl, 7 bedrooms, 4 bathrooms, 11 beds. Free parking for 10+ cars. Tesla charger.

House front view

Unit 1 Great room

Unit 1 Great room

Heavenly Killington

7 bedrooms·4 baths

Killington • Vermont

4.99(85 reviews)

2620,47 $ USD 2414,92 $ USD total por 3 noites

09/11/2026 – 12/11/2026

Glen Rd Mountain Retreat

3 bedrooms·2 baths

Peru • Vermont

1342,26 $ USD total por 3 noites

09/11/2026 – 12/11/2026

The private deck hot tub is included on peak-season weekends from late December to mid-March. Otherwise, optional use requires a $195 setup fee.

Choose a sofa by the windows, with the gas fireplace beside the seating area.

Cook in the full kitchen and bring meals straight to the table beside it.

The king bed sits beneath the single bed in the condo's one bedroom.

The living room opens toward the bedroom, with the gas fireplace beside the television.

Trailside Village 3 in Killington

1 bedroom·1 bath

Killington • Vermont

4.86(35 reviews)

1946,99 $ USD total por 3 noites

13/11/2026 – 16/11/2026

Off access rd Cozy Killington home Private Hot Tub image 1

Off access rd Cozy Killington home Private Hot Tub image 2

Off access rd Cozy Killington home Private Hot Tub image 3

Off access rd Cozy Killington home Private Hot Tub image 4

Off access rd Cozy Killington home Private Hot Tub image 5

Off access rd Cozy Killington home Private Hot Tub

2 bedrooms·2 baths

Killington • Vermont

4.96(45 reviews)

995,00 $ USD total por 3 noites

01/12/2026 – 04/12/2026

The private hot tub is included on peak-season weekends from late December to mid-March. Otherwise, arrange optional $195 setup with management.

The wood stove and two sofas share the main living space; firewood is supplied.

Use the private cedar sauna without leaving the condo.

Prepare meals in the kitchen, with a gas stove and dishwasher for cleanup.

The bedroom has a king bed, separate from the living room's sofa beds.

Trailside Village 1 in Killington

1 bedroom·1 bath

Killington • Vermont

5(25 reviews)

2001,37 $ USD total por 3 noites

09/11/2026 – 12/11/2026

The kitchenette sits just off the open sleeping area, beside the bathroom.

The bathroom opens beside the studio's sleeping area.

A lighted mirror and wall-mounted hair dryer are beside the bathroom sink.

The shower has an overhead showerhead and a handheld sprayer behind a glass door.

The bathroom's glass shower enclosure is just across from the kitchenette.

Killington Studio 541 with Kitchenette

0 bedrooms·1 bath

Killington • Vermont

4.63(30 reviews)

855,07 $ USD total por 3 noites

09/11/2026 – 12/11/2026