The Bennington County Court House with a white facade, green shutters, and a gold dome.

Winery Hotels & Resorts in Southern Vermont from AU$180

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Southern Vermont Winery Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Southern Vermont hotels with winery

A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.
A bar area with wooden ceiling, shelves with bottles, and a bar counter.
A multi-story hotel with balconies, a ski slope in the background, and a clear blue sky.
A dining area with a wooden table and chairs, a window with a view, and a bookshelf with books and decorative items.

1. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Jessica Louise
AU$180
includes taxes & fees
1 Nov - 2 Nov
Sun Lodge near Manchester VT, Ascend Collection Hotel
A red house with a white picket fence, surrounded by lush greenery and trees.
A bar area with a long counter, multiple stools, and a variety of bottles.
A gazebo, a red barn, and a white house in a garden with trees and flowers.
A buffet table with various food items and a decorative centerpiece.

2. Arlington Inn

Arlington Inn
Arlington
United States
Ann
AU$317
includes taxes & fees
18 Oct - 19 Oct
Arlington Inn
A spacious living area with a brown leather sofa, a wooden coffee table, and wicker chairs. A staircase leads to an upper level.
A cozy living room with a brown leather sofa, two wicker armchairs, a wooden coffee table, and a wooden chest.
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.
A view of a gravel driveway leading to a house with two Adirondack chairs on a grassy lawn.

3. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
United States
Brian S.
AU$655
includes taxes & fees
27 Oct - 28 Oct
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
An aerial view of a house surrounded by a forest with autumn foliage.
A bedroom with a bed, bedside table, lamp, and a ceiling fan.
A backyard with a campfire, two Adirondack chairs, and a house in the background.
A kitchen with white cabinets, a granite countertop, and a door leading to another room.

4. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
United States
Jonathan
AU$792
includes taxes & fees
28 Oct - 29 Oct
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Exterior
Living area
Exterior
Living area

5. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
United States
Lorraine C.
AU$1,023
includes taxes & fees
5 Oct - 6 Oct
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A modern two-story house with a front porch, a staircase, and a driveway.
An outdoor seating area with three Adirondack chairs and a fire pit.
A spacious living area with a dining table, chairs, and a kitchen in the background.
A spacious living area with a large sectional sofa, a coffee table, and a fireplace. There is a balcony with a view of greenery.

6. Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Jamaica
United States
Michael A.
AU$1,393
includes taxes & fees
26 Oct - 27 Oct
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
A red house with a porch, surrounded by a grassy yard and trees.
A house with a porch, a small pond, and surrounding trees.
A spacious living area with a wooden dining table, two bar stools, a kitchen area with white cabinets, and a television on a stand.
A modern kitchen with white cabinets, a granite countertop, and a dishwasher.

7. Two Brooks Lodge

Two Brooks Lodge
Bennington
United States
Hunter
Two Brooks Lodge
A sunroom with a large window, wicker furniture, and a fish mounted on the wall.
A spacious living area with a sofa, chairs, a television, and a fireplace.
A single-story house with a gabled roof, large windows, and a chimney.
A sunroom with a dining table and chairs, a cushioned bench with a patterned pillow, and large windows offering a view of a residential area.

8. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
United States
Jim V.
AU$600
includes taxes & fees
9 Oct - 10 Oct
Quaint, friendly cottage with lakefront location & water views
A modern kitchen with granite countertops, stainless steel appliances, and a central island.
A spacious kitchen with a central island, bar stools, and a fireplace.
A house with a porch, a front door with a wreath, and a mailbox.
A room with two leather chairs facing a large window with a stained glass design.

9. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
United States
Jeremy S.
AU$688
includes taxes & fees
26 Oct - 27 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A yurt with a red door, a visible interior with a fire, and snow outside.
A compact wooden cabin with a toilet, a small window, and a shelf with a bottle.
A traditional yurt with a patterned design, a wooden structure nearby, and a snowy landscape with trees.
A wooden outdoor seating area with a table and chairs, a grill, and a fire extinguisher.

10. Off-Grid Mongolian Yurt on Vermont Sheep Farm

Off-Grid Mongolian Yurt on Vermont Sheep Farm
Poultney
AU$219
includes taxes & fees
2 Nov - 3 Nov
Off-Grid Mongolian Yurt on Vermont Sheep Farm
View all properties

Top Southern Vermont Hotel Reviews

Explore a world of travel with Expedia