Title: Best Condo Resort Rental Windsor, MA for from $160 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## 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 condo resorts ![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) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.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) ### 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 $143 nightly $160 total Apr 11 - Apr 12 Total with taxes and fees [](https://www.expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26®ionId=6005427&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_6005427) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=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) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=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) Condos [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=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®ionId=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) Villas [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=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) Apartments [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=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) Chalets [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=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) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Condominium-Resort.d6005427-aaCondominiumResort.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Condominium-Resort.d6005427-aaCondominiumResort.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 6/10 Okay "The staff was friendly and the breakfast was great. The parking lots and grounds were unsafe. It's winter time and they should know better. Each time we went to our car we felt we were going to slip and fall. Same with the path from our room to the breakfast area. We came here for a relaxing baby moon and feared for our safety any time we left the room. When we arrived on a Thursday afternoon we were told the parking lots would soon be plowed. We left on a Sunday morning and neither had been touched the whole time we were there. The weather was rainy, then freezing, which makes for dangerous conditions if not treated properly. On one morning the parking lot was such a sheet of ice that we felt unsafe to drive and therefore had to abandon our planned morning activities. Throughout the stay we would see plenty of staff but they would not give an update on the plowing or even acknowledge the conditions of the lots or walkways." [](https://expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![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) ## Find out more about Windsor ## Windsor Condo Resorts information | Number of reviews | | | ----------------- | --------------- | | Accommodation | 2 Condo Resorts | | Lowest Price | $160 | | Highest Price | $160 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Cabin Rentals in Savoy ](https://www.expedia.com/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [B&B in Savoy ](https://www.expedia.com/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Savoy ](https://www.expedia.com/Savoy-Cottages.d6005417-aaCottages.Travel-Guide-Accommodation) - 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