A lake with a rocky shoreline and a forested island.

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Check availability on Western Massachusetts Romantic Hotels

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Western Massachusetts 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 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.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
￥21,330
￥33,357 total
includes taxes & fees
Oct 12 - Oct 13
Berkshire Village Carriage House - Super Private!!
A modern living room with a sofa, a coffee table, and a red patterned rug.
A narrow street flanked by two-story houses with a garage and a small tree.
A bedroom with a bed, a chair, a standing fan, and a mirror.
A modern kitchen with stainless steel appliances, including a refrigerator, oven, and microwave.

2. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
United States
Brian
￥26,307
￥53,867 total
includes taxes & fees
Oct 13 - Oct 14
Cozy & Spacious Entire Home in Springfield
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
￥36,182
￥75,889 total
includes taxes & fees
Oct 14 - Oct 15
A roomy remodeled retreat close to MassMoCA
A modern living room with a sofa, a coffee table, and a chair. There are two doors leading to other rooms.
A hallway with a cityscape mural, a table with a paint can, and a door leading to another room.
A dining area with a glass table and chairs, a pendant light, and a view of a hallway.
A hallway with a mirrored closet door, a bed with a patterned blanket, and a black chair.

4. Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
United States
Carol F.
￥43,798
￥80,879 total
includes taxes & fees
Oct 19 - Oct 20
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
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 cozy living room with a stone fireplace, leather sofas, a wooden coffee table, and a chandelier.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Rachel P.
￥21,330
￥39,382 total
includes taxes & fees
Oct 13 - Oct 14
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.
A hotel room with a large bed, a small table with a chair, and a window with curtains.
A house with a wooden front porch, a metal gate, and a sign that reads "Haven at Highlandlake."
A living room with a fireplace, a television mounted on the wall, a sofa, and a small round ottoman.

6. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
United States
traci
￥19,908
￥37,588 total
includes taxes & fees
Oct 12 - Oct 13
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A garden with a wooden pergola, purple flowers, and a river view.
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.
A living room with a brown sofa, a wooden coffee table, a dining table with chairs, and a staircase in the background.

7. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
United States
Susan G.
￥20,785
￥40,287 total
includes taxes & fees
Oct 20 - Oct 21
Family Friendly Hilltop House In Putney Vermont
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.

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.
￥9,738
￥48,362 total
includes taxes & fees
Oct 26 - Oct 27
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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.

9. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
￥19,987
￥45,221 total
includes taxes & fees
Oct 18 - Oct 19
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
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.
A wooden deck with a grill, a table, and chairs.

10. 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.
￥29,720
￥61,925 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
View all properties

Top Western Massachusetts Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Great hotel, comfortable, great breakfast"
Stefan 1-night trip
Posted 10 hours ago
D. Hotel Suites & Spa
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"We only stayed one night but it was clean, quiet and located in a safe area. Breakfast was very good and it being Free is a big bonus, esp with today’s prices! I have stayed at this chain before. Always enjoyed it and will continue to patronize this hotel. Thank you!!!"
Maria 1-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very spacious and clean room , at an affordable price vast of amenities surrounded by nature"
Rohit 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 1 day ago
The Red Lion Inn

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