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Featured Cottages in Windsor

Historic Huntington Home - Walk to Westfield River
Kitchen features a large window, refrigerator, stove, and dishwasher, with a ceiling fan for ventilation.

Historic Huntington Home - Walk to Westfield River

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful historical house in a rural setting. We were attending performances at Jacob’s Pillow. This house is approximately 20 minutes away, so very convenient."
Historic Huntington Home - Walk to Westfield River
Charlemont Retreat on Chickley River w/ EV Charger
Enjoy the serene surroundings and well-maintained deck adjacent to this house.

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Cavalier Cottage B&B
Exterior

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
Cavalier Cottage B&B
Cozy Becket Cottage Escape w/ Lake Access!
Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Relax on the porch amidst a serene garden and wooded surroundings, complete with a cozy fireplace.

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Spacious Historic Home in the Berkshires!
Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Relax in a serene garden setting surrounded by mature trees and lush greenery, with a stone fire pit and Adirondack chairs.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Interior

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
A-frame Cabin w/ Furnished Deck in Becket!
Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Luxury Vacation Rental in the Berkshires!
Enjoy cooking in this well-equipped kitchen with a range hood, double oven, and granite countertop.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Stockbridge Home: Walk to Town Beach!
Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Picturesque Cottage With Sunroom on Ashmere Lake!
Enjoy the serene view from the deck, where you can sit and relax with a wicker chair and table.

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Interior

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Lakefront Westhampton Cabin w/ Beach + Kayaks!
Interior

Lakefront Westhampton Cabin w/ Beach + Kayaks!

3.0 star property
Lakefront Westhampton Cabin w/ Beach + Kayaks!
12-acre Vacation Rental in the Berkshires!
Property grounds

12-acre Vacation Rental in the Berkshires!

3.0 star property
12-acre Vacation Rental in the Berkshires!
Massachusetts Vacation Rental w/ Deck & Grill
4 bedrooms, desk, laptop workspace, bed sheets

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
Elegant Pittsfield Home Near Downtown & Skiing!
Front of property

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
Stockbridge Retreat w/ Pool & Hot Tub!
Interior

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"The hotel was very unique as there was art spaces in the lobby. Liked that the room had lvp flooring. "
stephen 2-night trip
Posted 1 day ago
Hotel Downstreet, Ascend Hotel Collection

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between and per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Windsor with Expedia?
Expedia has some wonderful cottages in Windsor, so start packing your bags for a memorable holiday on nature's doorstep. If you have a budget in mind, select how much you'd like to spend and the star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We'll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Windsor?
Expedia is here to help you easily locate cheap cottages in Windsor. To reserve a fantastic stay in a few quick keystrokes, try out the filter tool to refine your search results by amenities, star rating and budget.