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Find Romantic Hotels in The Berkshires, MA

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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 house with a brick exterior, a green roof, and a driveway leading to a garage.
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.
£161
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 spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.
A covered outdoor deck with a wooden table and a mug, overlooking a forested area.
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.
£490
includes taxes & fees
22 Oct - 23 Oct
Secluded Family Home in Serene Stockbridge Woods
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A cozy room with a wooden bench, a small table, and a chair.
A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.
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
Diane
£364
includes taxes & fees
31 Oct - 1 Nov
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.
£207
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 cozy living room with a sectional sofa, a coffee table, and a ceiling fan.
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.

5. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
£213
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 living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.
A cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.

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
£400
includes taxes & fees
29 Oct - 30 Oct
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.

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.
£293
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 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.

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.
£243
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 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.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.

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.
£1,084
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 dining area with a wooden table and chairs, a chandelier, a fireplace, and a kitchen in the background.
A spacious living room with a fireplace, a dining area, and a kitchen with wooden cabinets and a microwave.

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.
£506
includes taxes & fees
22 Oct - 23 Oct
Experience Vermont’s Fall Magic at here at the Lemondrop
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Find out more about The Berkshires

The Berkshires attractions for couples

The Berkshires is a paradise of experiences waiting to be explored. Start your adventure at the renowned Tanglewood Music Center, where you can enjoy a summer concert by the Boston Symphony Orchestra amidst the stunning natural backdrop. For art enthusiasts, the Massachusetts Museum of Contemporary Art (MASS MoCA) is a must-visit, showcasing groundbreaking installations and performances in a former mill turned vibrant art hub. Families will delight in a day at the Berkshire Museum, where interactive exhibits and a diverse aquarium offer fun for all ages. Outdoor lovers can hike the picturesque trails of Mount Greylock, the highest peak in Massachusetts, breathtaking panoramic views and well-maintained paths suitable for all skill levels. After a day of exploration, unwind in the charming town of Lenox, known for its luxurious accommodations like the historic Cranwell Spa & Golf Resort. With its elegant rooms and top spa services, it’s the perfect base for a comfortable stay while you delve into the region's rich culture and natural beauty. The Berkshires promises a delightful blend of artistic flair and outdoor adventure, ensuring memorable experiences for the entire family.

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This is hands down my favorite hotel, and I have stayed here before and will keep coming back again and again! Everything about this place makes it feel special. The rooms are always spotless, incredibly spacious, and equipped with everything you need to feel right at home. Having a coffee maker, a full-size refrigerator, an oven, and a stove makes such a difference, especially for longer stays. The excellent jacuzzi is another big plus and makes it easy to relax and unwind. The property also has so many great amenities, and the surrounding nature is absolutely beautiful. There are plenty of amazing places to explore nearby, making it a perfect destination for a relaxing getaway while still having lots of things to do. What I love most is that the rooms feel more like a fully equipped apartment than a typical hotel room. It’s the kind of place where you can truly settle in, feel comfortable, and wish you could stay longer. I absolutely love this hotel, and it will always be one of my favorite places to stay. I will definitely be back again and again!"
Diana 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 1 day ago
Hampton Inn & Suites Berkshires-Lenox

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