Windsor Holiday Rentals

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Check prices for these dates

Tonight
28 Oct - 29 Oct
Tomorrow
29 Oct - 30 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Windsor

Lobby
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2110)
"Great place!"
United States
Nicole
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (984)
"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."
United States
Amy
The price is HK$1,157
HK$1,293 total
includes taxes & fees
30 Oct - 31 Oct
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The Ponds at Foxhollow
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
United States
Stephanie R.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,653
HK$8,630 total
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$3,146
HK$5,996 total
includes taxes & fees
4 Nov - 5 Nov
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Bear Creek Cabin
Bear Creek Cabin
10.0 out of 10, Exceptional, (41)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,107
HK$4,651 total
includes taxes & fees
4 Nov - 5 Nov
Bear Creek Cabin
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (32)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Interior
Charming 3-bedroom Cabin for nature lovers
Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is HK$1,023
HK$2,257 total
includes taxes & fees
11 Nov - 12 Nov
Charming 3-bedroom Cabin for nature lovers
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is HK$1,251
HK$3,747 total
includes taxes & fees
30 Oct - 31 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Interior
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.8 out of 10, Exceptional, (19)
"Rich is more than a Super Host! We were welcomed personally upon arrival and given a tour of the property and grounds. Nestled in lush nature, the view of the lake while rocking in the swinging bench is breathtaking. Very clean and comfortable accommodations. "
United States
Vicki M.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Smart TV, fireplace, DVD player, music library
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
9.4 out of 10, Exceptional, (84)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
United States
Elizabeth R.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Dining
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.6 out of 10, Exceptional, (16)
"We came for a concert at Tanglewood. Property was just as photos described, walking distance to downtown Lee restaurants, easy access to highway and other towns. Great spot for multiple family or friends to get together."
United States
Karyn P.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (69)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.8 out of 10, Exceptional, (46)
"Home is lovely, fun bedroom themes."
United States
Kate H.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Property grounds
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
9.8 out of 10, Exceptional, (70)
"Beautiful location, very spacious, comfortable and clean."
United States
Aubrey G.
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (229)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
United States
Donald G.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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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Top Windsor Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Excellent all the way around"
Kevin 3-night trip
Posted 21 hours ago
Berkshire Mountain Lodge

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its restaurants and shopping.

What are some of the best holiday rentals that Windsor has to offer?

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox: This holiday home rental outside Windsor is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation Visitor Center. Mount Greylock and Barrington Stage Company are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.