A lake with a rocky shoreline and a forested island.

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Check availability on Western Massachusetts Romantic Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
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 dog lying on a stone wall in a forested area.
A house with a brick exterior, a green roof, and a driveway leading to a garage.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
￥21,318
￥33,338 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 dining area with a glass table, grey chairs, and a vase of white flowers. There is a green upholstered chair, a chandelier, and a painting of a rose on the wall.
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
￥26,337
￥53,928 total
includes taxes & fees
Oct 12 - Oct 13
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
￥36,223
￥76,682 total
includes taxes & fees
Oct 13 - Oct 14
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 dining area with a glass table and chairs, a pendant light, and a view of a hallway.
A hallway with a cityscape mural, a table with a paint can, and a door leading to another room.
A modern kitchen with granite countertops, stainless steel appliances, and a walk-in pantry.

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.
￥44,559
￥81,959 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 bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A cozy living room with a stone fireplace, leather sofas, a wooden coffee table, and a chandelier.
A cozy living room with a stone wall, a fireplace, and a chandelier.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Rachel P.
￥21,354
￥39,426 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 round table with two chairs, a wine glass, and a cup on a tray.
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
￥19,931
￥37,631 total
includes taxes & fees
Oct 8 - Oct 9
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 living room with a brown sofa, a wooden coffee table, a dining table with chairs, and a staircase in the background.
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, and a window with blinds.

7. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
United States
Susan G.
￥21,034
￥40,537 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 modern kitchen with stainless steel appliances, a wooden dining table, and light-colored cabinetry.

9. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
￥20,010
￥41,568 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 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.

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.
￥29,703
￥62,416 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
View all properties

Top Western Massachusetts Hotel Reviews

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 16 hours 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 18 hours ago
The Red Lion Inn
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"Great staff,Spotless facility decent price"
William 1-night trip
Posted 23 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

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