Location

Dates

Guests

Vacation rentals in Cavendish, Vermont, United States

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)

$1,375.00 USD total for 5 nights

Sep 7 – 12, 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)

$1,375.00 USD total for 5 nights

Sep 7 – 12, 2026

Property grounds

Reading Farms Estate Front Lawns

Reading Farms Estate

15 bedrooms·10 baths

Reading • Vermont

$12,292.00 USD total for 3 nights

Sep 7 – 10, 2026

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

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 for 5 nights

Sep 13 – 18, 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/ night(excl. fees & taxes)

Enjoy the expansive views from our cozy living room

Mountain View Manor

King of the Hill views from the firepit

Chef's Kitchen and seating for 12

Read a book while swinging in our hammock chairs

Mountain View Manor

6 bedrooms·5 baths

Windsor County • Vermont

$3,966.87 USD total for 3 nights

Oct 1 – 4, 2026

Free cancellation

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(85 reviews)

$1,097.47 USD total for 3 nights

Sep 7 – 10, 2026

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

Hot Tub Area
Undercover!

Hot Springs Hot Tub ~ seats 4

King Master Bedroom

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

2 bedrooms·3 baths

Plymouth • Vermont

5(31 reviews)

$1,695.00 USD total for 3 nights

Sep 8 – 11, 2026

We are currently updating our photos.
Front lawn view

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

Vermont Cottage Amherst Lake & Sanctuary

6 bedrooms·4 baths

Plymouth • Vermont

4.98(90 reviews)

$6,582.00 USD total for 6 nights

Sep 15 – 21, 2026

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

Historic Vermont Lake Cottage~Hot Tub~Dogs~Okemo

4 bedrooms·3 baths

Plymouth • Vermont

5(55 reviews)

$2,294.20 USD total for 3 nights

Sep 7 – 10, 2026

The front porch at dusk

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

Cute Cabin! Plymouth, Vermont.

3 bedrooms·3 baths

Plymouth • Vermont

5(52 reviews)

$2,031.00 USD total for 3 nights

Sep 8 – 11, 2026

Get-Away Cabin in Plymouth, Vermont.

Aerial view of Lake Amherst

Large screened-in porch overlooking the lake.

Get-Away Cabin in Plymouth, Vermont.

Get-Away Cabin in Plymouth, Vermont.

1 bedroom·2 baths

Plymouth • Vermont

5(34 reviews)

$1,107.00 USD total for 3 nights

Sep 7 – 10, 2026

1930s-era cottage.

Private outdoor hot tub under cover.

Outdoor fire pit

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

The living room opens up to a larger screened-in porch. Dining also on the porch. It features a wood-burning fireplace for cooler times. It will be all set to light and we provide plenty of wood.

Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs

1 bedroom·2 baths

Plymouth • Vermont

$1,191.00 USD total for 3 nights

Sep 7 – 10, 2026

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

Vermont Mountain Chalet • Hot Tub • Near Skiing

4 bedrooms·3½ baths

Plymouth • Vermont

$1,497.62 USD total for 3 nights

Oct 27 – 30, 2026

Free cancellation

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/ night(excl. fees & taxes)

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Sep 7 – 10, 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)

$1,745.18 USD $1,507.29 USD total for 3 nights

Sep 7 – 10, 2026

Enjoy a crackling fire in our living room and open kitchen

Jacuzzi Tub Added July '23

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 2 (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

$2,572.72 USD total for 3 nights

Sep 7 – 10, 2026

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

Exterior view of House. Stairs from Driveway and Deck.

Dining Room with chairs for 8

Dining Room. Sliding door with access to east deck & gas Grill

Fully equipped kitchen. New stainless steel look appliances

Leather sofa and love seat

Private House with Fantastic Views off Home Stretch Trail

4 bedrooms·2 baths

Killington • Vermont

5(48 reviews)

$2,750.00 USD total for 4 nights

Sep 7 – 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)

$209 – $309/ night(excl. fees & taxes)

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(24 reviews)

$3,565.96 USD $3,274.27 USD total for 3 nights

Sep 11 – 14, 2026