---
title: "Best Apartments in Windsor, MA for Your Vacation from $154 | Expedia"
description: "Find the best Apartments in Windsor, MA in 2026. Compare rates from $154, guest reviews and availability of 0 stays. Most stays are fully refundable."
canonical: "https://www.expedia.com/Windsor-Apartments.d6005427-aaApartments.Travel-Guide-Accommodation"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-15T15:42:19Z
---

Plan your trip

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

# Apartments in Windsor for Rent

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### Upfront pricing
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## Find vacation rentals that suit your style

[Cabins](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=CABIN)

[Apartments](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=APARTMENT)

[Aparthotels](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=APART%5FHOTEL)

[Condos](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=CONDO)

[Cottages](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=COTTAGE)

[Villas](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=VILLA)

[Chalets](https://www.expedia.com/Hotel-Search?destination=Windsor,%20Massachusetts,%20United%20States%20of%20America&regionId=6005427&latLong=42.509022,-73.045715&adults=2&startDate=2026-11-22&d1=2026-11-22&endDate=2026-11-24&d2=2026-11-24&lodging=CHALET)

## Check prices for these dates

[Check prices for these dates, December 15 – 16, 2026](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-12-15&endDate=2026-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&lodging=APARTMENT)

[View in a map](https://www.expedia.com/Hotel-Search?regionId=6005427&stayLength=1&daysInFuture=30&pwaOverlay=map)

## Our top choices for Windsor apartments

### [1\. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton](https://www.expedia.com/Dalton-Hotels-Bright.h107876022.Hotel-Information)

![A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.](https://images.trvl-media.com/lodging/108000000/107880000/107876100/107876022/20a59d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

- Location: Dalton
- Guest rating: 9.8/10 (Exceptional, 35 reviews)
- Price: $268 nightly, $299 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!, by Marcia O.

### [2\. Penthouse Apartment on Park Street](https://www.expedia.com/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information)

![A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/c64df1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Adams
- Guest rating: 9.6/10 (Exceptional, 19 reviews)
- Price: $238 nightly, $266 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Great penthouse apartment with interesting artwork throughout. Location convenient to local attractions; a five minutes easy drive to Mass MOCA. The apartment was impeccably clean and the host was very responsive to questions we had during our stay. Would love to stay again., by Lisa M.

### [3\. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor](https://www.expedia.com/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

![A cozy living room with a large window, wooden walls, and a television.](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/8313bf81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 10/10 (Exceptional, 6 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! , by Maura D.

### [4\. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated](https://www.expedia.com/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information)

![A fire pit with chairs, a ski lift, and a building with a sign that reads "Mountain Resort".](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 10/10 (Exceptional, 6 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly., by Ann

### [5\. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown](https://www.expedia.com/North-Adams-Hotels-Perfect-2-Bedroom-Apartment-With-AC-In-Peaceful-North-Adams.h125667585.Hotel-Information)

![A garden with various plants, a brick wall, and a cactus in pots.](https://images.trvl-media.com/lodging/126000000/125670000/125667600/125667585/fcdbdab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Adams
- Guest rating: 8/10 (Very good, 2 reviews)
- Price: $179 nightly, $200 total, Nov 18 - Nov 19, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again., by Ruthie K.

### [6\. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone](https://www.expedia.com/Hancock-Hotels-Must-See-Cabin-Suite-Jiminy-Sleeps-4-Mountainview-Ski-OnOff-Country-Inn-Redone.h90182167.Hotel-Information)

![A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.](https://images.trvl-media.com/lodging/91000000/90190000/90182200/90182167/ba182761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 10/10 (Exceptional, 14 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Staying right in the mountain was ideal. The condo was perfect. , by patricia f.

### [7\. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor](https://www.expedia.com/Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

![A snow-covered outdoor area with a fire pit, seating, and a building in the background.](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/w1280h856x0y0-65161e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 10/10 (Exceptional, 3 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Stayed one night at one of my favorite ski spots. Will be back again!, by Neil J.

### [8\. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn](https://www.expedia.com/Hancock-Hotels-Gorgeous-Zen-Must-See-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h83121139.Hotel-Information)

![A hotel room with a bed, a desk, a television, a window with curtains, and artwork on the walls.](https://images.trvl-media.com/lodging/84000000/83130000/83121200/83121139/b0d0405c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 9.4/10 (Exceptional, 19 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended., by David

### [9\. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base](https://www.expedia.com/Hancock-Hotels-Ski-OnOff-1BR-SUITE-SLEEPS-4-Best-Location-Jiminy.h69537711.Hotel-Information)

![A living room with a television, sofa, coffee table, and a painting of trees.](https://images.trvl-media.com/lodging/70000000/69540000/69537800/69537711/861cddd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 9.6/10 (Exceptional, 33 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. , by Eileen O.

### [10\. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor](https://www.expedia.com/Hancock-Hotels-Deluxe-Mountain-Fox-Suite-Jiminy-Peak-Ski-On-Off-Fully-Redone-Decor.h101424483.Hotel-Information)

![A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.](https://images.trvl-media.com/lodging/102000000/101430000/101424500/101424483/b5600d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 10/10 (Exceptional, 2 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Great place, everything was so easy!!, by Dana

### [11\. Relaxing 1-bedroom apartment in North Adams](https://www.expedia.com/North-Adams-Hotels-Relaxing-1-Bedroom-Apartment-In-North-Adams.h138722930.Hotel-Information)

![A bedroom with a bed, nightstands, and a ceiling fan.](https://images.trvl-media.com/lodging/139000000/138730000/138723000/138722930/efb28c64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Adams
- Price: $138 nightly, $154 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments

### [12\. New Studio In Town, By the Water](https://www.expedia.com/Williamstown-Hotels-New-Studio-In-Town.h45471406.Hotel-Information)

![A wooden deck with Adirondack chairs, a fire pit, and a view of a forested area with a stream.](https://images.trvl-media.com/lodging/46000000/45480000/45471500/45471406/e12673e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Williamstown
- Guest rating: 10/10 (Exceptional, 21 reviews)
- Review: Great location, we really enjoyed our stay! , by Lydia J.

### [13\. 2 Twin beds on 1st floor with En-suite bathroom.](https://www.expedia.com/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information)

![A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/9832d1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Shelburne Falls
- Price: $153 nightly, $171 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments

### [14\. Berkshires Apartment at the Stephentown Hotel](https://www.expedia.com/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.Hotel-Information)

![A modern bathroom with a glass-enclosed shower, black marble tiles, a wooden vanity, and a white sink.](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/1cad06d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Stephentown
- Guest rating: 10/10 (Exceptional, 6 reviews)
- Price: $198 nightly, $210 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!, by Nicole O.

### [15\. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views](https://www.expedia.com/Hancock-Hotels-Gorgeous-2BR-2BA-Condo-At-Jiminy-Peak-W-Mtn-Views.h130297518.Hotel-Information)

![A deck with a table and chairs, a barbecue grill, and a view of a green landscape.](https://images.trvl-media.com/lodging/131000000/130300000/130297600/130297518/6ebbad86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 8/10 (Very good, 1 review)
- Price: $244 nightly, $273 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: "I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on..., by Cecilia S.

### [16\. Downtown | Waterfront | Walk to Shops](https://www.expedia.com/Williamstown-Hotels-Downtown-Waterfront-Walk-To-Shops.h101733841.Hotel-Information)

![A wooden deck with Adirondack chairs, a fire pit, and a view of a forested area with a stream.](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733841/8e7a5ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Williamstown
- Guest rating: 9.8/10 (Exceptional, 13 reviews)
- Price: $256 nightly, $289 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Great location, very clean, included washer dryer, picnic area by river, large parking space., by Douglas

### [17\. 2-Bdr Apt In Town, By the Water](https://www.expedia.com/Williamstown-Hotels-2-Bdr-Apt-In-Town.h101733845.Hotel-Information)

![A wooden deck with Adirondack chairs, a fire pit, and a view of a forested area with a stream.](https://images.trvl-media.com/lodging/102000000/101740000/101733900/101733845/7b0ebc77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Williamstown
- Guest rating: 9.2/10 (Wonderful, 23 reviews)
- Price: $258 nightly, $290 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: Perfect check in process, spotlessly clean, gorgeous property, and I wish I had had enough time to relax by the water. Best experience I've had, and I will definitely stay there again., by Andrea

### [18\. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center](https://www.expedia.com/Lenox-Hotels-Find-1-Bedroom-Apartment-In-Tranquil-Lenox-3-Minutes-From-Tanglewood-Music-Hall.h133547366.Hotel-Information)

![A covered outdoor seating area with two chairs and a view of a grassy landscape.](https://images.trvl-media.com/lodging/134000000/133550000/133547400/133547366/858f39b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Lenox
- Price: $259 nightly, $289 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Windsor apartments

### [19\. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn](https://www.expedia.com/Hancock-Hotels-SKI-ONOFF-1BR-SUITE-1ST-FLR-SLEEPS-4-JIMINY-PEAK.h69787457.Hotel-Information)

![A living room with a sofa, armchair, coffee table, TV, and a window with curtains.](https://images.trvl-media.com/lodging/70000000/69790000/69787500/69787457/cc5c53f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Hancock
- Guest rating: 9.8/10 (Exceptional, 25 reviews)
- Price: $190 nightly, $213 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Windsor apartments
- Review: We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!, by Kristina L.

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://www.expedia.com/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30&regionId=6005427&adults=2&sort=VACATION%5FRENTAL&openPlayBack=true)

## Top reviews in Windsor

### [Harbour House Inn](https://www.expedia.com/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

![A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/83f2a35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Cheshire
- Review: The Harbor House Inn is a wonderfully situated B and B, located 8 miles south of North Adams. The welcome is warm, and amenities are generous. Highly recommended., by Anonymous traveler, June 26, 2017, rated 10/10 Excellent

### [Hotel On North](https://www.expedia.com/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information)

![A multi-story hotel with a classic facade, large windows, and a prominent entrance.](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pittsfield
- Review: The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and..., by Steve, February 28, 2016, rated 10/10 Excellent

### [The Revival House](https://www.expedia.com/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information)

![A bedroom with a bed, a sofa, a fireplace, and a chandelier.](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/674accb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Adams
- Review: Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7, by Ruby, November 9, 2026, rated 10/10 Excellent

### [The Porches Inn at Mass MoCA](https://www.expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information)

![Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/5d23ad0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Adams
- Review: Absolutely lovely. Bed was super comfortable, staff was friendly and helpful, lots of places to sit and relax. Easy walk to restaurants and across the street from the MOCA. Nice breakfast and you can even get a drink and a snack in the evening if you want. The sauna, whirlpool and heated pool at the end of October we a pleasant surprise., by Stacey, November 1, 2024, rated 10/10 Excellent

### [The Trail in Adams - Berkshires’ Art Hotel](https://www.expedia.com/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information)

![A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/48c1cff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Adams
- Review: The house was very unique. Everything was perfect. The room was the nicest I've stayed in!!!, by Esther, October 7, 2023, rated 10/10 Excellent

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

![Two Adirondack chairs facing a river with a forested hill in the background.](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/a4d29137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Lenox
- Review: We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!, by Colleen, July 17, 2024, rated 10/10 Excellent

### [Hotel Downstreet, an Ascend Collection Hotel](https://www.expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information)

![A reception area with a large landscape painting, a dark reception desk, and a potted plant.](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/a866db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: North Adams
- Review: Great place!, by Ann, May 12, 2025, rated 10/10 Excellent

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

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/76732b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Williamstown
- Review: Clean , comfortable place to stay after skiing all day., by Anonymous traveler, March 7, 2016, rated 10/10 Excellent

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

![A spacious lobby with a fireplace, multiple seating areas, and a chandelier.](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pittsfield
- Review: It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues., by Elliott, December 5, 2024, rated 10/10 Excellent

### [Hilton Garden Inn Lenox Pittsfield](https://www.expedia.com/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

![A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b3b1ec3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Pittsfield
- Review: The staff could not have been more helpful, great location and the facility extremely clean. We were shocked about how amazing this place was, by t, January 18, 2016, rated 10/10 Excellent

### [Element by Marriott Lenox Berkshires](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

![A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Lenox
- Review: Clean and spacious room., by Richard, November 12, 2026, rated 10/10 Excellent

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

![A spacious hotel lobby with multiple seating areas, large windows, and a television.](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Lenox
- Review: Solid, by Colton, January 29, 2025, rated 10/10 Excellent

### [The Cornell Inn, Lenox & The Berkshires](https://www.expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

![A snow-covered outdoor area with a patio, seating, and a covered dining area.](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Lenox
- Review: VERY friendly staff and location for area attractions., by Lawrence, February 12, 2023, rated 10/10 Excellent

### [Maple Terrace Motel](https://www.expedia.com/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information)

![A garden with a swing set, a blue chair, and a flower bed.](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Williamstown
- Review: Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates., by Eric, May 2, 2024, rated 10/10 Excellent

### [Courtyard by Marriott Lenox Berkshires](https://www.expedia.com/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information)

![An outdoor patio area with a circular fire pit surrounded by wicker furniture and a stone fire table.](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Lenox
- Review: Room was so nice. Bed was comfortable. Overall glad we stayed here., by Alyssa, May 18, 2024, rated 10/10 Excellent

### [Willows Motel Williamstown](https://www.expedia.com/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information)

![A white two-story building with a porch, labeled as a motel.](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/dccac924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
- Location: Williamstown
- Review: This motel is in a convenient location for visiting Williams College. Rooms are clean and the mattresses are very comfortable. They have the largest TV screens I've seen in any motel. Their Continental breakfast is extensive with a variety of pastries, breads, and beverages. The staff is kind, caring, helpful, and accommodating., by Sandra, April 17, 2018, rated 10/10 Excellent

## Frequently Asked Questions

### What's it like to stay at an apartment in Windsor?

You might not have many choices centrally in Windsor, but Expedia can help you find lodging options in the area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. You can even filter by similar properties such as condos, vacation homes, or cottages.

### Are you thinking about an apartment for your stay?

An apartment features a kitchen for convenient meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families who want the conveniences of home.

### What's a favorite apartment for a stay in Windsor?

Here are some of the top apartments in the area to choose from: [FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!](https://www.expedia.com/Pownal-Hotels-FARM-TO-TABLE-Eating.h33998602.Hotel-Information): Located in Pownal, 21.6 mi/34.8 km from the heart of Windsor. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are on site. [Downtown | Waterfront | Walk to Shops](https://www.expedia.com/Williamstown-Hotels-Downtown-Waterfront-Walk-To-Shops.h101733841.Hotel-Information): Located 15.8 mi/25.5 km away in Williamstown. Free WiFi, private balconies, and sofa beds are included. A fitness center and onsite laundry facilities are on site. [Cozy 1-bedroom apartment in old farm house in historic South Lee](https://www.expedia.com/South-Lee-Hotels-Cozy-1-Bedroom-Apartment-In-Old-Farm-House-In-Historic-South-Lee.h126796997.Hotel-Information): Located in South Lee, 20.1 mi/32.3 km away. Includes private patios. Access to onsite laundry facilities is available on site. [Quiet Neighborhood, For Bird Lovers](https://www.expedia.com/South-Deerfield-Hotels-Quiet-Neighborhood.h34012910.Hotel-Information): 21.2 mi/34.2 km away in South Deerfield.

### What can I expect from the weather during my trip to Windsor?

Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay in Windsor. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

### What should I see and do in Windsor?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Wahconah Falls State Park. In the larger area, you’ll find Mount Greylock State Reservation Visitor Center and Pontoosuc Lake.

### What's the best way to get to and around Windsor?

Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 13.8 mi (22.2 km) away from the city center. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

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