Location

Dates

Guests

Vacation rentals in Winhall, Vermont, United States

Open comfy space with wide floor boards and spiral access to the large loft.

Relax by the gas fireplace on second floor

The 1827 House has easy access from RT 100 where you can walk to fine restaurants and venture to close by Wilmington, Manchester and lots of trails!

Comfortable and romantic Queen Victorian room

Loft Queen beds

Historic 1827 House | 3BR • AC • Upstairs

3 bedrooms·2 baths

Dover • Vermont

5(28 reviews)

$862.50 USD total for 3 nights

Sep 7 – 10, 2026

The Great Room was once the village general store and Post Office. Imagine the conversations over the years in this room.

Easy access on RT100.

Upstairs living area. Views of mount snow ski area from north side windows.

Futon in Loft sleeps two. Great for overflow skiers.

Relax by the gas fireplace on second floor after a day of skiing. Mini Split for quiet & comfortable AC in the summer and heat in the winter.

Historic 1827 House | 5BR • AC • Walkable

5 bedrooms·3 baths

Dover • Vermont

5(20 reviews)

$1,710.00 USD total for 3 nights

Sep 7 – 10, 2026

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

The Riverside Treehouse

3 bedrooms·2 baths

Arlington • Vermont

5(4 reviews)

$889.69 USD total for 3 nights

Sep 7 – 10, 2026

Front yard and house

Guard rails have been added both sides of stairs since this picture was taken.

Looking up toward loft area with partial view of kitchen lower right. Note the spiral staircase.

Cozy converted barn on secluded 6.5 acres

3 bedrooms·1 bath

Shaftsbury • Vermont

5(390 reviews)

$916.60 USD total for 3 nights

Sep 22 – 25, 2026

Open concept living and dining room; plenty of seating at the dinner table

Top of the Rock

View of the house from the backyard

A winter snowfall

Our driveway can easily fit 2-3 cars

Top of the Rock

4 bedrooms·2 baths

Wilmington • Vermont

4.77(13 reviews)

$1,045.00 USD total for 3 nights

Sep 7 – 10, 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(85 reviews)

$1,097.47 USD total for 3 nights

Sep 7 – 10, 2026

Luxe VT Retreat • Perfect for Remote Summer Stays

Luxe VT Retreat • Perfect for Remote Summer Stays

Luxe VT Retreat • Perfect for Remote Summer Stays

Luxe VT Retreat • Perfect for Remote Summer Stays

Luxe VT Retreat • Perfect for Remote Summer Stays

Luxe VT Retreat • Perfect for Remote Summer Stays

3 bedrooms·2 baths

Newfane • Vermont

4.5(2 reviews)

$9,369.15 USD total for 30 nights

Oct 1 – 31, 2026

Free cancellation

Riverside Getaway + Wood-Fired Sauna

Riverside Getaway + Wood-Fired Sauna

Riverside Getaway + Wood-Fired Sauna

Riverside Getaway + Wood-Fired Sauna

Riverside Getaway + Wood-Fired Sauna

Riverside Getaway + Wood-Fired Sauna

0 bedrooms·1 bath

Newfane • Vermont

$639.45 USD total for 3 nights

Oct 1 – 4, 2026

Free cancellation

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

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Sep 7 – 10, 2026

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

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)

Charming Home with Lake and Mountain View

Charming Home with Lake and Mountain View

Charming Home with Lake and Mountain View

Charming Home with Lake and Mountain View

Charming Home with Lake and Mountain View

Charming Home with Lake and Mountain View

5 bedrooms·3 baths

Whitingham • Vermont

$1,562.02 USD total for 3 nights

Sep 7 – 10, 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 for 5 nights

Sep 13 – 18, 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

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)

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

Looking back up at the house with the lake behind you.

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

View of the house and garage as you turn into the driveway from the private road leading up to our home.

View from across Little Lake

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

3 bedrooms·3½ baths

Wells • Vermont

4.98(95 reviews)

$1,387.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Free cancellation

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