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

Romantic Hotels & Resorts in Southern Vermont from NZ$363

  • 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 Romantic Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Southern Vermont romantic hotels

A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.
A compact living space with a brown leather sofa, a dining table with chairs, a kitchen area, and a fireplace.
A compact kitchen with a wooden table and chairs, a white countertop, and light green cabinets.
A bunk bed room with a patterned rug, a window, and a bedside table.

1. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
United States
Tania J.
NZ$533
includes taxes & fees
28 Sept - 29 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A red house with a covered porch and a chimney.
Two single beds with wooden frames and striped bedding, a small wooden nightstand with a lamp, and a window with a view of greenery.
A kitchen with a wooden table and chairs, a microwave, and cabinets.
A living room with a wood-burning stove, a blue armchair, and a bookshelf.

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
NZ$628
includes taxes & fees
30 Sept - 1 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A pathway through a forest with autumn leaves and a wooden bridge.
A fireplace with visible logs and flames, a wooden table with a plate of cookies, a bowl of marshmallows, and a glass of red wine.
A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.
A dining area with a wooden table and chairs, a chandelier, a fireplace, and a kitchen in the background.

3. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
United States
Alexander H.
NZ$1,118
includes taxes & fees
25 Sept - 26 Sept
Experience Vermont’s Fall Magic at here at the Lemondrop
A garden with purple flowers and a river in the background.
A living room with a brown sofa, a wooden coffee table, a dining table with chairs, and a staircase in the background.
A living room with a brown sofa, a wooden coffee table, and a window with blinds.
A two-story wooden cabin with a balcony, a red door, and a star decoration.

4. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
United States
Susan G.
NZ$455
includes taxes & fees
30 Sept - 1 Oct
Family Friendly Hilltop House In Putney Vermont
A large estate with a swimming pool, tennis court, and a spacious lawn.
A spacious living room with leather sofas, a coffee table with a fruit bowl, and a patterned rug.
A person sitting on a stone ledge outdoors with a scenic view in the background.
A large indoor swimming pool with a wooden interior, multiple windows, and seating areas.

5. The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
Manchester
United States
Jessica G.
NZ$3,705
includes taxes & fees
21 Oct - 22 Oct
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.
A two-story house with a front porch, a small garden, and a mailbox.
A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.

6. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
United States
Anita T.
NZ$692
includes taxes & fees
29 Sept - 30 Sept
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.
A dog lying on a stone wall in a forested area.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

7. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
NZ$363
includes taxes & fees
30 Sept - 1 Oct
Berkshire Village Carriage House - Super Private!!
A wooden cabin with a red roof, a balcony, and a staircase leading to the upper level.
A rustic wooden interior with a large circular window, wooden beams, and a hanging lantern.
A rustic cabin interior with a wooden staircase, a globe, a refrigerator, and a window with a view of trees.
A wooden cabin with a deck and stairs, surrounded by trees and a sunset.

8. Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing

Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
Munsonville
United States
Ryan W.
NZ$578
includes taxes & fees
29 Sept - 30 Sept
Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
A backyard with picnic tables and Adirondack chairs, a wooden fence, and a red building in the background.

9. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
NZ$498
includes taxes & fees
18 Oct - 19 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.
A cozy room with a wooden bench, a small table, and a chair.
A room with a wooden bench, a table, and a door with glass panels.

10. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
NZ$844
includes taxes & fees
14 Oct - 15 Oct
A roomy remodeled retreat close to MassMoCA
View all properties

Top Southern Vermont Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Muy conveniente y cerca del bike park"
Omar 2-night trip
Posted 10 hours ago
The Black Bear Lodge at Stratton Mountain Resort
The Manchester View

The Manchester View

10/10 Excellent
"Very cool unique setting and property. The bed was like a cloud and very relaxing."
David B 1-night trip
Posted 15 hours ago
The Manchester View
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 23 hours ago
The Equinox Golf Resort And Spa
The White House Inn

The White House Inn

10/10 Excellent
"This is a great place to stay with a beautiful hotel and beautiful views from the hotel. The staff is great and the manager went out of his way to make sure our stay went well."
John 1-night trip
Posted 3 days ago
The White House Inn

Explore a world of travel with Expedia