Airbnb, Vacation Rentals in Windsor, MA

Compare 1,034 available, short term lakefront holiday vacation home properties, starts from $28

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Airbnb, Vacation rentals and hotel deals in Windsor, MA

FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
9.4 (68 reviews)
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
Apartment · 2 Guests · 1 Bedroom
$185 /night*
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Cozy and quaint country cottage, walk to downtown Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown
9.2 (82 reviews)
Cozy and quaint country cottage, walk to downtown Williamstown
Holiday home · 2 Guests · 1 Bedroom
$133 /night*
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The Red Lion Inn
The Red Lion Inn
The Red Lion Inn
The Red Lion Inn
8.5 (290 reviews)
The Red Lion Inn
Hotel · 2 Guests · 1 Bedroom
$119 /night
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Berkshire Mountain Lodge
Berkshire Mountain Lodge
Berkshire Mountain Lodge
Berkshire Mountain Lodge
8.6 (130 reviews)
Berkshire Mountain Lodge
Lodge · 2 Guests · 1 Bedroom
$165 /night
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Villager Motel
Villager Motel
Villager Motel
Villager Motel
8.6 (537 reviews)
Villager Motel
Motel · 2 Guests · 1 Bedroom
$69 /night
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Stockbridge Home: Walk to Town Beach!
Stockbridge Home: Walk to Town Beach!
Stockbridge Home: Walk to Town Beach!
Stockbridge Home: Walk to Town Beach!
10 (2 reviews)
Stockbridge Home: Walk to Town Beach!
Holiday home · 2 Guests · 1 Bedroom
$173 /night*
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Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
10 (40 reviews)
Quiet Neighborhood, For Bird Lovers
Apartment · 2 Guests · 1 Bedroom
$150 /night*
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Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
6.7 (114 reviews)
Pleasant Valley Motel West Stockbridge
Motel · 2 Guests · 1 Bedroom
$59 /night
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Cozy apartment located in quiet Williamsburg
Cozy apartment located in quiet Williamsburg
Cozy apartment located in quiet Williamsburg
Cozy apartment located in quiet Williamsburg
9.6 (28 reviews)
Cozy apartment located in quiet Williamsburg
Holiday home · 2 Guests · 1 Bedroom
$150 /night*
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Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
8.4 (224 reviews)
Best Western Plus Berkshire Hills Inn & Suites
Hotel · 2 Guests · 1 Bedroom
$110 /night
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WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
8.2 (175 reviews)
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
Holiday home · 2 Guests · 1 Bedroom
$189 /night
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Hotel on North
Hotel on North
Hotel on North
Hotel on North
9.4 (187 reviews)
Hotel on North
Hotel · 2 Guests · 1 Bedroom
$166 /night
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Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
9.3 (227 reviews)
Courtyard by Marriott Lenox Berkshires
Hotel · 2 Guests · 1 Bedroom
$163 /night
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Willows Motel
Willows Motel
Willows Motel
Willows Motel
9.1 (148 reviews)
Willows Motel
Motel · 2 Guests · 1 Bedroom
$75 /night
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The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
9.0 (471 reviews)
The Yankee, Trademark Collection by Wyndham
Hotel · 2 Guests · 1 Bedroom
$83 /night
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Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
6.2 (474 reviews)
Econo Lodge Lee - Great Barrington
Motel · 2 Guests · 1 Bedroom
$58 /night
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The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA
9.3 (85 reviews)
The Porches Inn at Mass MoCA
Inn · 2 Guests · 1 Bedroom
$141 /night
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A simple kind of paradise
A simple kind of paradise
A simple kind of paradise
A simple kind of paradise
10 (12 reviews)
A simple kind of paradise
Agritourism · 2 Guests · 1 Bedroom
$195 /night*
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Blooming Inn
Blooming Inn
Blooming Inn
Blooming Inn
8.6 (29 reviews)
Blooming Inn
Guest house · 2 Guests · 1 Bedroom
$66 /night
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Pilgrim Inn
Pilgrim Inn
Pilgrim Inn
Pilgrim Inn
6.2 (59 reviews)
Pilgrim Inn
Inn · 2 Guests · 1 Bedroom
$69 /night
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Vacation Destinations Near Windsor, MA

Airbnb, Holiday Lakefront House with Air Conditioning in Windsor, MA

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
Air Conditioning
8.2 (175 reviews)
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk
Holiday home · 2 Guests · 1 Bedroom
$189 /night
View deal
The Trail in Adams - Berkshires' Art Hotel
The Trail in Adams - Berkshires' Art Hotel
The Trail in Adams - Berkshires' Art Hotel
The Trail in Adams - Berkshires' Art Hotel
Air Conditioning
9.5 (12 reviews)
The Trail in Adams - Berkshires' Art Hotel
B & B · 2 Guests · 1 Bedroom
$214 /night
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Gateways Inn
Gateways Inn
Gateways Inn
Gateways Inn
Air Conditioning
7.8 (10 reviews)
Gateways Inn
B & B · 2 Guests · 1 Bedroom
$254 /night
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What Are The Most Popular Amenities in Windsor, MA?
Best Amenities in Windsor, MA
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Check above for the most common and the least popular rental amenities in Windsor, and pick the one that fits your preference easily. In Windsor, 488 rentals offer Internet or Wifi, 471 rentals offer No Smoking, 464 rentals offer Bed linens provided. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Most Typical in Windsor, MA Area?
Vacation House & Condo Rental Price Information in Windsor, MA
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The graph shows the percentages of vacation homes in each price bucket. Windsor has the largest percentage (14.98%) of homes in $150 - $200 price range.
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$500 +
$500 +
What Are The Popular Property Types in Windsor, MA?
Top Rental Accommodations in Windsor, MA
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There are various types of homes in Windsor area. Depending on your group size, you can pick the one using filters accordingly. House is the most popular accommodation type, and the largest homes can accommodate 38 people.The least popular accommodation in Windsor is Mill rentals
How Many Accommodations Are Pets Allowed in Windsor, MA?
Percentage of Pet Friendly Rental Properties in Windsor, MA
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31.14% of vacation homes in Windsor are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Must-Visit Trails in Windsor, MA?
Best Trails In Windsor, MA
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The most visited trails here in Windsor are: Orange Trail, Pink Trail, Tannery Falls Trail, Appalachian Trail: Dalton to Cheshire, Cheshire Cobbles Trail, The Cobbles Via Appalachian Trail, William Cullen Bryant Homestead Trail, Notchview Reservation, Old Mill Trail, Wahconah Falls.
Where Are The Campgrounds in Windsor, MA Area?
Campgrounds Recommendations In Windsor, MA
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The best RV campgrounds here in Windsor are: Alps Family Campground, Broken Wheel Campground, Aqua Vista Campground, Woodland Hills Campground, Pine Hollow Campground, Clarksburg Campground, Tolland State Forest Campground, Northampton / Springfield KOA, Mohawk Trail State Forest Campground, Indian Hollow Campground.
What are the Airports in Windsor, MA?
Top Airports in Windsor, MA
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Here are the airports that located near Windsor:

Airbnb, Holiday Lakefront House with Full Kitchen, and Other Rental Options in Windsor, MA

Beautiful four season lakeside log home close to all Berkshires attractions.
Beautiful four season lakeside log home close to all Berkshires attractions.
Beautiful four season lakeside log home close to all Berkshires attractions.
Beautiful four season lakeside log home close to all Berkshires attractions.
Full Kitchen
9.8 (38 reviews)
Beautiful four season lakeside log home close to all Berkshires attractions.
Holiday home · 2 Guests · 1 Bedroom
$395 /night*
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Cozy and quaint country cottage, walk to downtown Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown
Cozy and quaint country cottage, walk to downtown Williamstown
Full Kitchen
9.2 (82 reviews)
Cozy and quaint country cottage, walk to downtown Williamstown
Holiday home · 2 Guests · 1 Bedroom
$133 /night*
View deal
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
Full Kitchen
9.6 (20 reviews)
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
Holiday home · 2 Guests · 1 Bedroom
$755 /night*
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Airbnb, Vacation Condo with Pool, and Other Rental Options in Windsor, MA

FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
Pool
9.4 (68 reviews)
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!
Apartment · 2 Guests · 1 Bedroom
$185 /night*
View deal
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Quiet Neighborhood, For Bird Lovers
Pool
10 (40 reviews)
Quiet Neighborhood, For Bird Lovers
Apartment · 2 Guests · 1 Bedroom
$150 /night*
View deal
Recently Updated Condo at Jiminy Peak
Recently Updated Condo at Jiminy Peak
Recently Updated Condo at Jiminy Peak
Recently Updated Condo at Jiminy Peak
Pool
10 (2 reviews)
Recently Updated Condo at Jiminy Peak
Condo · 2 Guests · 1 Bedroom
$350 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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