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

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Check availability on The Berkshires Romantic Hotels

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 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.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
€193
includes taxes & fees
22 Oct - 23 Oct
Berkshire Village Carriage House - Super Private!!
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.
A covered outdoor deck with a wooden table and a mug, overlooking a forested area.
A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.
A green house with a porch, surrounded by a garden with various plants and flowers.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
€611
includes taxes & fees
2 Nov - 3 Nov
Secluded Family Home in Serene Stockbridge Woods
A kitchen with white cabinets, a wooden dining table, and pendant lights.
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.
A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
€434
includes taxes & fees
30 Oct - 31 Oct
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 staircase with a stone wall on one side and a wooden handrail on the other.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
€247
includes taxes & fees
5 Nov - 6 Nov
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.
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 modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
A backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.

5. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
€255
includes taxes & fees
25 Oct - 26 Oct
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 room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
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.

6. 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
€479
includes taxes & fees
29 Oct - 30 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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.
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.

7. 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.
€350
includes taxes & fees
22 Oct - 23 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 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.

8. 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.
€291
includes taxes & fees
26 Oct - 27 Oct
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A modern kitchen with white cabinets, a large island, and a skylight.
A wooden cabin with a deck and stone steps, surrounded by a grassy area and trees.
A bedroom with a large bed, a red rug, a bookshelf, and a chair.
A two-story house with a gravel driveway leading to a garage.

9. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
United States
stephen r.
€1,294
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
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.

10. 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.
€601
includes taxes & fees
22 Oct - 23 Oct
Experience Vermont’s Fall Magic at here at the Lemondrop
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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Fantastic stay everyone was Fantastic"
paul 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."
Melissa 1-night trip
Posted 22 hours ago
Hampton Inn & Suites Berkshires-Lenox

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