Location

Dates

Guests

Vacation rentals in Winhall, Vermont, United States

Hillside Getaway

Hillside Getaway

Hillside Getaway

Hillside Getaway

Hillside Getaway

Hillside Getaway

3 bedrooms·2 baths

Sandgate • Vermont

5(17 reviews)

$1,480.90 USD total for 3 nights

Nov 17 – 20, 2026

Table is made from reclaimed barn wood and great for a large dinner.

Steps to Farm Rd Estate | Historic 2BR w/ AC! image 2

Relax with some art or watch a great movie in the Great Room on the comfy sofa.

Reclaimed barnwood table

The large bedroom on the first floor was transformed from the art gallery.

Historic 1827 House | 2BR • Walkable location

2 bedrooms·1 bath

Dover • Vermont

5(61 reviews)

$1,920.18 USD total for 3 nights

Mar 19 – 22, 2027

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)

$969.85 USD total for 3 nights

Nov 17 – 20, 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)

$500 – $750/ night(excl. fees & taxes)

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)

$944.42 USD total for 3 nights

Nov 18 – 21, 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)

$866.20 USD $793.96 USD total for 3 nights

Nov 30 – Dec 3, 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)

$1,210.00 USD total for 3 nights

Nov 17 – 20, 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)

$1,097.47 USD $934.75 USD total for 3 nights

Nov 17 – 20, 2026

The Ravens Nest

3 bedrooms·1 bath

Woodford • Vermont

$797.68 USD total for 3 nights

Nov 17 – 20, 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

2 bedrooms·2 baths

Newfane • Vermont

4.5(2 reviews)

$959.70 USD total for 3 nights

Nov 17 – 20, 2026

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

$493.50 USD total for 3 nights

Nov 17 – 20, 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

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$927.00 USD total for 3 nights

Nov 17 – 20, 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/ 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

$1,663.99 USD total for 3 nights

Nov 17 – 20, 2026

Charming Home with Lake and Mountain View

Cozy winter retreat with a spacious deck and serene snowy surroundings

Charming Home with Lake and Mountain View

Peaceful snowy landscape with stunning mountain views

Charming Home with Lake and Mountain View

Charming Home with Lake and Mountain View

5 bedrooms·3 baths

Whitingham • Vermont

$1,501.25 USD total for 3 nights

Nov 17 – 20, 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

Nov 17 – 22, 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)

$1,104.88 USD total for 5 nights

Nov 17 – 22, 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)

$1,104.88 USD total for 5 nights

Nov 17 – 22, 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

5(126 reviews)

$1,387.00 USD total for 3 nights

Jan 18 – 21, 2027

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)

$1,705.00 USD total for 3 nights

Nov 17 – 20, 2026

Twilight ~ CURRENTLY UPDATING PICTURES ~ STAY TUNED!

Screened-in Front Porch

Vermont Cottage Amherst Lake & Sanctuary

4 bedrooms·3 baths

Plymouth • Vermont

5(70 reviews)

$2,294.20 USD total for 3 nights

Nov 17 – 20, 2026

The front porch at dusk

Cute Vermont Cabin! Plymouth, Vermont.

Cute Vermont Cabin! Plymouth, Vermont.

Cute Vermont Cabin! Plymouth, Vermont.

Cute Vermont Cabin! Plymouth, Vermont.

3 bedrooms·3 baths

Plymouth • Vermont

5(52 reviews)

$2,031.00 USD total for 3 nights

Nov 17 – 20, 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)

$1,191.00 USD total for 3 nights

Nov 17 – 20, 2026