A person snowboarding down a snowy slope.

The Berkshires Hotel Guide - Romantic Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Romantic Hotels

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for The Berkshires romantic hotels

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
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.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
€202
includes taxes & fees
16 Sept - 17 Sept
Berkshire Village Carriage House - Super Private!!
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.
A hot tub with four people, wooden walls, and wall-mounted lights.
A snow-covered outdoor area with a fire pit, tables, and chairs, indicating a winter resort setting.

2. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
United States
John F.
€215
includes taxes & fees
7 Sept - 8 Sept
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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 room with a wooden bench, a table, and a door with glass panels.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
€408
includes taxes & fees
9 Sept - 10 Sept
A roomy remodeled retreat close to MassMoCA
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.
A cozy living room with a stone wall, a fireplace, and a chandelier.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A staircase with a stone wall on one side and a wooden handrail on the other.

4. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
€220
includes taxes & fees
9 Sept - 10 Sept
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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 two-story building with a steeply pitched roof, a front door, and a staircase leading to a deck.
A compact kitchen with a wooden table and chairs, a white countertop, and light green cabinets.

5. 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.
€270
includes taxes & fees
14 Sept - 15 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Cherry Plain State Park with a sandy beach, people relaxing, and a lake.
A cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
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.

6. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
€257
includes taxes & fees
7 Sept - 8 Sept
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A patio with a table and chairs, a grill, and a view of a lake.
A cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.
A living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.
A two-story house with a garage, a driveway, and a river in the background.

7. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
United States
Mike
€459
includes taxes & fees
10 Sept - 11 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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 two-story house with a front porch, a small garden, and a mailbox.

8. 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.
€342
includes taxes & fees
8 Sept - 9 Sept
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.
A cozy interior with a fireplace, wooden walls, and a chandelier.
A rustic kitchen with wooden shelves, a gas stove, an oven, and a microwave.
A loft-style room with a wooden ceiling, exposed beams, and a view of the outside through large windows.

9. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
€313
includes taxes & fees
8 Sept - 9 Sept
rural, serene + sophisticated space
A pathway through a forest with autumn leaves and a wooden bridge.
A residential area with houses, a driveway, and a hilly landscape in the background.
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 dining area with a wooden table and chairs, a chandelier, a fireplace, and a kitchen in the background.

10. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
United States
Alexander H.
€557
includes taxes & fees
15 Sept - 16 Sept
Summer Escape Near Lakes, Trails & Mt Snow
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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Enjoyed our stay and would highly recommend!"
Roger 2-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Great little motel that was the perfect stay for a quick overnight trip"
Kate 1-night trip
Posted 4 hours ago
Willows Motel Williamstown
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."
Colleen And mark 2-night trip
Posted 1 day ago
The Red Lion Inn

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