Title: Windsor Vacation Rentals from $141: Search Short-Term Rentals | Expedia.com

[Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor vacation rentals

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

Williamstown

8.8/10

Excellent

(2,295 reviews)

"Excellent location and terrific space and amenities."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

$126 nightly

$141 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/5d56a155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/708e6bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/539e07bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554000/98553938/c1c12e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 12-acre Vacation Rental in the Berkshires!

[](https://www.expedia.com/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.Hotel-Information)

Charlemont

$515 nightly

$545 total

Mar 13 - Mar 14

Total with taxes and fees

[](https://www.expedia.com/Charlemont-Hotels-12-Acre-Vacation-Rental-In-The-Berkshires.h98553938.Hotel-Information)

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

[](https://www.expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

Hancock

8.2/10

Very Good

(989 reviews)

"nice and clean, good customer service, but the room is smell. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Huang

$148 nightly

$166 total

Apr 10 - Apr 11

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/a965b40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/65ba1b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Huttopia Berkshires 

[](https://www.expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

Williamstown

9.4/10

Exceptional

(10 reviews)

"Healthy food too!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

GEORGINA

$147 nightly

$165 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/0800588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

Stephentown

$499 nightly

$554 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

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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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CABIN)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=VILLA)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CONDO)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-06-09&d1=2026-06-09&endDate=2026-06-12&d2=2026-06-12&lodging=CHALET)

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## Top Windsor Hotel Reviews

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"the room was huge - we loved it!!"

[](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"In the process of remodeling, but my room which was already renovated was very nice, as was the breakfast room. "

[](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4_y.jpg)

### Red Roof Inn PLUS+ South Deerfield – Amherst

4/10 Poor

"The property was clean but the beds were very uncomfortable. They need to replace the mattresses."

[](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information)

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Great place in Williamstown. Near ski resort."

[](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"This place is okay. The view is stellar, but the hotel itself is average. It did the job. "

[](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"This area is really starting to build up. There is a small ski area. An Italian restaurant and 110 grill right on that road. About 15 min away Applebees. A lot of pizza and Mexican. Winter not only is there skiing there are a lot of snowmobile trails. Summer there are water falls you can see. Tubing you can do. The mountains are beautiful. Quiet and relaxing. "

[](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

6/10 Okay

"Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good look or feel for those staying there. Maybe in six months or a year down the line, hotel will come back to its glory. Today still needs lots of work. "

[](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_y.jpg)

### Huttopia Berkshires 

10/10 Excellent

"Excelente servicio "

[](https://expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Room was awesome and very clean "

[](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

## Find out more about Windsor

**Everything you need to know about Windsor vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Windsor vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Windsor rentals**

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Vacation Homes in Windsor ](https://expedia.com/Windsor-Private-Vacation-Homes.d6005427-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Windsor ](https://expedia.com/Windsor-Apartments.d6005427-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Windsor ](https://expedia.com/Windsor-Cottages.d6005427-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Windsor ](https://expedia.com/Windsor-Condos.d6005427-aaCondos.Travel-Guide-Accommodation)
- [B&B in Windsor ](https://expedia.com/Windsor-Bed-And-Breakfast.d6005427-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Windsor ](https://expedia.com/Windsor-Resorts.d6005427-aaResorts.Travel-Guide-Accommodation)
- [Motels in Windsor ](https://expedia.com/Windsor-Motels.d6005427-aaMotels.Travel-Guide-Accommodation)
- [Farmstay in Windsor ](https://expedia.com/Windsor-Agritourism.d6005427-aaAgritourism.Travel-Guide-Accommodation)
- [Cabin Rentals in Windsor ](https://expedia.com/Windsor-Cabins.d6005427-aaCabins.Travel-Guide-Accommodation)
- [Guest Houses in Windsor ](https://expedia.com/Windsor-Guest-Houses.d6005427-aaGuestHouses.Travel-Guide-Accommodation)
- [Chalets in Windsor ](https://expedia.com/Windsor-Chalets.d6005427-aaChalets.Travel-Guide-Accommodation)
- [Inns in Windsor ](https://expedia.com/Windsor-Inns.d6005427-aaInns.Travel-Guide-Accommodation)
- [Villas in Windsor ](https://expedia.com/Windsor-Villas.d6005427-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Windsor ](https://expedia.com/Windsor-Lodges.d6005427-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Windsor ](https://expedia.com/Windsor-Apart-Hotels.d6005427-aaApartHotels.Travel-Guide-Accommodation)
- [Condo Resorts in Windsor ](https://expedia.com/Windsor-Condominium-Resort.d6005427-aaCondominiumResort.Travel-Guide-Accommodation)
- [RV Parks in Windsor ](https://expedia.com/Windsor-RV-Parks.d6005427-aaRVParks.Travel-Guide-Accommodation)
- [Castles in Windsor ](https://expedia.com/Windsor-Castles.d6005427-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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