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Find Romantic Hotels in Windsor, MA from CA $154

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Check availability on Windsor Romantic Hotels

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

Our top choices for Windsor romantic hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
CA $138
CA $154 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
A patio area with outdoor furniture, a fire pit, and potted plants.
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".
A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

2. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
CA $150
CA $165 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
CA $184
CA $206 total
includes taxes & fees
Nov 16 - Nov 17
Berkshires Untold
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."

4. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
United States
Ram
CA $222
CA $279 total
includes taxes & fees
Nov 15 - Nov 16
The Porches Inn at Mass MoCA
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.
A lodge with a large building and a dock by a lake, surrounded by forest.

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
CA $162
CA $181 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
CA $218
CA $250 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

7. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Steven
CA $177
CA $194 total
includes taxes & fees
Nov 16 - Nov 17
Shaker Mill Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

8. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
CA $223
CA $319 total
includes taxes & fees
Nov 8 - Nov 9
The Red Lion Inn
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.
A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.
A wooden interior with a table, chair, and a view of a red barn through an open door.

9. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Linda
CA $246
CA $276 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Silver Maple Farm
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A dining table set with a vase of flowers, a book, and cutlery.
A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

10. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
CA $275
CA $319 total
includes taxes & fees
Nov 15 - Nov 16
Brook Farm Inn
View all properties

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The staff was very helpful. The were lots of activities offered including the pool, hot tub, movie theater , and renting movies for free. The unit was very spacious and comfortable. We could hear the people above us stomping around a bit but that’s to be expected."
Jessica 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Good stay"
Jared 1-night trip
Posted 9 hours ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort
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 2 days ago
The Cornell Inn, Lenox & The Berkshires

Frequently asked questions

Searching for romantic hotels in Windsor?
Are you looking for a romantic escape? If you want to see some sights and attractions in the greater Windsor area, you might head to Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, or Pontoosuc Lake. If you're interested in staying close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Windsor?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Windsor: The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Windsor?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Windsor has to offer. If you're interested in seeing some of the area's sights and attractions, you might make a stop at Wahconah Falls State Park or Mount Greylock State Reservation Visitor Center.
What's the best way to get to Windsor and around town during my romantic getaway?
These transportation options in Windsor might help your romantic getaway go off without a hitch: To get to Windsor, you can fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport, located 13.8 mi (22.2 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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