Find Extended Stay Hotels in Windsor, MA

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Top Windsor Extended Stay Hotels | Reserve now, pay later

Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (434)
"Nice place, easy check in"
United States
Robert
$101 nightly
The price is $111
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
Front of property
Blooming Inn

Blooming Inn

3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (117)
"When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else."
United States
christian
$139 nightly
The price is $150
Nov 11 - Nov 12
Total with taxes and fees
Blooming Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (751)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
$113 nightly
The price is $126
Nov 11 - Nov 12
Total with taxes and fees
Berkshire Mountain Lodge
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (583)
"Pool, fire pit, grounds and staff were great!"
United States
Kristy
$99 nightly
The price is $111
Nov 13 - Nov 14
Total with taxes and fees
Maple Terrace Motel
Courtyard
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (85)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$101 nightly
The price is $111
Nov 18 - Nov 19
Total with taxes and fees
The Springs Motel
Smart TV, Netflix, streaming services
In town, newly remodeled studio with private balcony

In town, newly remodeled studio with private balcony

Shelburne Falls
10.0 out of 10, Exceptional, (119)
"Lovely apartment, perfect for a short getaway for city slickers. Close to town. The apartment was great, came well-equipped and everything was as described. The deck was lovely to spend a slow morning having breakfast. "
United States
Megan N.
$131 nightly
The price is $146
Nov 23 - Nov 24
Total with taxes and fees
In town, newly remodeled studio with private balcony
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (341)
"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"
United States
Candee
$85 nightly
The price is $95
Nov 11 - Nov 12
Total with taxes and fees
The Central Downtown Inn & Suites
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2131)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
$112 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
$121 nightly
The price is $136
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Exterior
Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg
10.0 out of 10, Exceptional, (31)
"Beautiful, quaint farmhouse in Williamsburg. Perfect for our family of 4 for a one night stay while passing through the area on a long drive. House was clean and just as advertised. Very comfortable beds! Would definitely recpmmend if in the area."
United States
Brynn Crawford L.
$342 nightly
The price is $362
Nov 11 - Nov 12
Total with taxes and fees
Charming, updated 3 bedroom farmhouse farm stay.
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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Frequently asked questions

Why book an extended stay hotel in Windsor through Expedia?
Book an extended stay hotel in Windsor through Expedia and you're certain to save. Along with our unbeatable offers and reward programs, we make finding the ideal long-term stay a cinch. Use our filter tool to search for accommodations based on location, family-friendly amenities, price range and more. Some long-term rentals may offer weekly rates to help keep more dollars in your pocket. Usually equipped with homey conveniences like a laundry and kitchen, your next extended stay in Windsor is just a few clicks away!
What can I expect from an extended stay hotel?
Reserve an extended stay hotel in Windsor and take as much time as you need getting to know this popular destination. On top of being able to stay a few weeks or longer, these types of properties come with conveniences designed to make your trip an easy one. Kitchens, laundries and recreational facilities are just the beginning. To find the perfect extended stay hotel, use Expedia's filters to fine-tune your search based on amenities, price range and more. Often offering competitive weekly rates, extended stay hotels can be less expensive than your standard hotel option.

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We came here because it was off season, great price, and it had an indoor pool. "
Monica 3-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
Amy 2-night trip
Posted 1 month ago
Jiminy Peak Mountain Resort

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