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

Find Romantic Hotels in Southern Vermont, VT

  • 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
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Southern Vermont romantic hotels

A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.
A two-story building with a steeply pitched roof, a front door, and a staircase leading to a deck.
A bunk bed room with a patterned rug, a window, and a bedside table.
A compact living space with a brown leather sofa, a dining table with chairs, a kitchen area, and a fireplace.

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.
AED 226
AED 1,156 total
includes taxes & fees
26 Oct - 27 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A garden with a wooden pergola, purple flowers, and a river view.
A living room with a brown sofa, a wooden coffee table, and a window with blinds.
A room with a large window offering a view of a grassy landscape with trees and a distant mountain range.
A two-story wooden cabin with a balcony, a red door, and a star decoration.

2. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
United States
Susan G.
AED 483
AED 931 total
includes taxes & fees
20 Oct - 21 Oct
Family Friendly Hilltop House In Putney Vermont
A red house with a covered porch and a chimney.
A kitchen with white cabinets, a microwave, a stove, and a sink.
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.

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
AED 624
AED 1,329 total
includes taxes & fees
14 Oct - 15 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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 house with a brick exterior, a green roof, and a driveway leading to a garage.

4. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
AED 496
AED 775 total
includes taxes & fees
19 Oct - 20 Oct
Berkshire Village Carriage House - Super Private!!
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.
A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.
A wooden deck with a grill, a table, and chairs.

5. 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.
AED 691
AED 1,452 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 wooden cabin with a red roof, surrounded by lush greenery and a clear sky.
A wooden cabin with a deck and stairs, surrounded by trees and a sunset.

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

Handcrafted NH Treehouse · 2hr Boston · Fire Pit, Lake, Stargazing
Munsonville
United States
Ryan W.
AED 826
AED 1,188 total
includes taxes & fees
18 Oct - 19 Oct
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 backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.
A red building with a green door labeled "Apartment 1," a small garden with mulch and plants, and a white car parked in the background.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.

7. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
AED 424
AED 996 total
includes taxes & fees
15 Oct - 16 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.
A room with a wooden bench, a table, and a door with glass panels.
A cozy room with a wooden bench, a small table, and a chair.

8. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
AED 841
AED 1,772 total
includes taxes & fees
14 Oct - 15 Oct
A roomy remodeled retreat close to MassMoCA
View all properties

Top Southern Vermont Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"The"
LISA 2-night trip
Posted 7 hours ago
The White House Inn
The Manchester View

The Manchester View

8/10 Good
"Beautiful room, very clean and new. It was very bare in the room though. Breakfast from 8-10 and we went at 9:40, it was wiped out with nobody refilling so make sure you go early. Next day we went early and it was delicious! Hot tub was amazing which we used both nights. Overall, the views are gorgeous and highly recommend this hotel."
Marybeth 2-night trip
Posted 15 hours ago
The Manchester View
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"It's a great place to stay! I've been there several times in different seasons. Off-season or leaf peeper season the free breakfast is a lot less than the free breakfast during ski season. During ski season AKA winter, eggs, waffles, pancakes etc however during other seasons they only offer cold cereal, milk bagels toast and juice and coffee of course. Other than that it's a fantastic place and they're dog friendly"
Bridget 1-night trip
Posted 2 days ago
The Black Bear Lodge at Stratton Mountain Resort
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Great place my wife and I enjoyed our stay."
Ian 2-night trip
Posted 6 days ago
Kimpton Taconic Hotel by IHG

Explore a world of travel with Expedia