Location

Dates

Guests

Vacation rentals in Rutland, Vermont, United States

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/ nacht(excl. kosten & belastingen)

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 totaal voor 3 nachten

27–30 okt 2026

Carriage House

2 bedrooms·2 baths

Mount Holly • Vermont

$ 927,00 USD totaal voor 3 nachten

23–26 okt 2026

Front of the home from the two-car off street parking pad. Walkway lights up at night for later check-ins.

Cute, Renovated Home on River, Walk to Downtown

Cute, Renovated Home on River, Walk to Downtown

Spacious upstairs full bath

Cute, Renovated Home on River, Walk to Downtown

Cute, Renovated Home on River, Walk to Downtown

3 bedrooms·1½ baths

Brandon • Vermont

4.8(51 reviews)

$ 788,00 USD totaal voor 3 nachten

26–29 okt 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

$350/ nacht(excl. kosten & belastingen)

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 totaal voor 3 nachten

26–29 okt 2026

We are currently updating our photos.
Front lawn view

Vermont Cottage Amherst Lake

Vermont Cottage Amherst Lake

Vermont Cottage Amherst Lake

Vermont Cottage Amherst Lake

6 bedrooms·4 baths

Plymouth • Vermont

4.98(90 reviews)

$ 6.582,00 USD totaal voor 6 nachten

24–30 okt 2026

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)

$ 2.294,20 USD totaal voor 3 nachten

26–29 okt 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)

$ 1.919,00 USD totaal voor 3 nachten

26–29 okt 2026

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

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

Hot Tub Area
Undercover!

Hot Springs Hot Tub ~ seats 4

King Master Bedroom

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

2 bedrooms·3 baths

Plymouth • Vermont

5(31 reviews)

$ 1.593,00 USD totaal voor 3 nachten

26–29 okt 2026

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

Lake Saint Catherine Cottage with Private Dock

2 bedrooms·2 baths

Poultney • Vermont

$ 1.488,21 USD totaal voor 3 nachten

23–26 okt 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)

$ 1.139,00 USD totaal voor 3 nachten

24–27 okt 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 totaal voor 3 nachten

25–28 okt 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)

$ 2.184,00 USD totaal voor 3 nachten

24–27 okt 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 totaal voor 5 nachten

23–28 okt 2026

View of the mountains and forest from the living room

Front of the cabin as seen from the lawn in late summer.

Winter sunset behind our cabin.

Catch "golden hour" from the fire pit as the sunset illuminates the mountains to the east.

Early May rainbow

Goshen Getaway: Cabin with Stunning Mountain Views

3 bedrooms·1 bath

Goshen • Vermont

5(90 reviews)

$ 776,60 USD totaal voor 3 nachten

26–29 okt 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 $ 934,75 USD totaal voor 3 nachten

25–28 okt 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 totaal voor 5 nachten

24–29 okt 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 totaal voor 5 nachten

24–29 okt 2026

Property grounds

Reading Farms Estate Front Lawns

Reading Farms Estate

15 bedrooms·10 baths

Reading • Vermont

$ 12.292,00 USD totaal voor 3 nachten

23–26 okt 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)

$ 3.418,00 USD $ 2.538,70 USD totaal voor 3 nachten

23–26 okt 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)

$ 1.695,78 USD $ 1.467,77 USD totaal voor 3 nachten

23–26 okt 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