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Check availability on The Berkshires Romantic Hotels

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 modern kitchen with white cabinets, a granite countertop, and a central island with stools.
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.

1. 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 spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.
A house with a covered porch and a well-maintained garden.
A green house with a porch, surrounded by a garden with various plants and flowers.
A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.

2. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
AED 1,253
AED 2,372 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
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.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
AED 841
AED 1,764 total
includes taxes & fees
26 Oct - 27 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 fireplace, leather sofas, a wooden coffee table, 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.
AED 551
AED 994 total
includes taxes & fees
2 Nov - 3 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 backyard with a wooden fence, a fire pit, and several Adirondack chairs in blue and white.
A modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.
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.

5. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
AED 465
AED 1,047 total
includes taxes & fees
18 Oct - 19 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 cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.
A room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
A two-story house with a garage, a driveway, and a river in the background.

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
AED 1,146
AED 1,942 total
includes taxes & fees
19 Oct - 20 Oct
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A modern kitchen with white cabinets and a built-in knife block.

7. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,074
AED 2,240 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A two-story house with a front porch, a small garden, and a mailbox.
A wooden deck with a grill, a table, and chairs.
A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.

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.
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 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 bunk bed room with a patterned rug, a window, and a bedside table.
A two-story building with a steeply pitched roof, a front door, and a staircase leading to a deck.

9. 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 1,164 total
includes taxes & fees
19 Oct - 20 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.

10. 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.
AED 2,920
AED 4,961 total
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
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Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Wonderful"
Philippe 2-night trip
Posted 4 hours ago
The Red Lion Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."
Benjamin 2-night trip
Posted 21 hours ago
The Cornell Inn, Lenox & The Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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