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Compare 21 Farmstay in Windsor with updated reviews, rates, and availability.

Charming Farmhouse - quiet, private & peaceful

9.6 out of 10, Exceptional, (61)
"The property was great, and the owner was super responsive. I would definitely rate this property excellent if it was a little cleaner. Loved the quiet and peacefulness! "
Charming Farmhouse - quiet, private & peaceful

Berkshire Rural Retreat

10.0 out of 10, Exceptional, (19)
"Wonderful spot, quiet and secluded but still close to a ton of stuff! Great kitchen and house, easy for 4 adults and 4 kids. Lots to do outside also. Would recommend and will look to stay again if we’re out in the Berkshires again!"
Berkshire Rural Retreat

Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

9.6 out of 10, Exceptional, (14)
"Apartment was clean, bright with comfortable beds. Great location for Berkshires visit, close to Tanglewood and all places fun. Only drawback for us (me and two college friends) was that we brought food for breakfasts and it’s not set up for eating in. No sink in the small kitchen so paper plates and plastic utensils are provided. Small but useful refrigerator. Only a microwave. Small coffee maker but Jodi nicely provided lots of coffee so we weren’t ornery in the morning! Brought in picnic food...
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!

Experience a charming 3 bedroom farm stay close to winter activity.

10.0 out of 10, Exceptional, (25)
"Nice quiet location. Very clean and friendly host. Kids loved the animals and the swing set. Only issue is single bath which is on the first floor bedrooms all upstairs."
The price is AED 754
AED 1,228 total
includes taxes & fees
7 Jan - 8 January 2025
Experience a charming 3 bedroom farm stay close to winter activity.

Large, family-friendly farmhouse located in the beautiful Berkshires

9.8 out of 10, Exceptional, (31)
"The Hart's family have a beautiful home full of wonderful historical artifacts, comfortable furniture, and well stocked kitchen and bathrooms. We loved the wide plank floors, working fireplace, and modern day wifi. Thank you for sharing this wonderful property."
Large, family-friendly farmhouse located in the beautiful Berkshires

Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.

9.0 out of 10, Wonderful, (2)
"A very quaint and well appointed house in a lovely neighborhood."
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.

Play Area, Crib, 11 Acre Farmhouse

10.0 out of 10, Exceptional, (7)
"The nearly 200-year old Carley Farmhouse nestled amidst the Vermont hills is a real keeper! The natural beauty of the area is stunning, and nature lovers will appreciate the bird chatter, occasional monarch butterfly, starry skies, complete with fireflies in the yard! Gather chairs around the firepit in the yard at night and enjoy it all. Inside, there are several living areas including a small back sunporch that is a quiet retreat both during the day and at night. We didn't end up using the...
Play Area, Crib, 11 Acre Farmhouse

Stunning views on 545 acres at end of dirt road

10.0 out of 10, Exceptional, (48)
"This house and property are amazing! Everything was clean, well stocked and there were even hiking trails. Owners were easy to communicate with and helpful!"
Stunning views on 545 acres at end of dirt road

Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.

9.8 out of 10, Exceptional, (10)
"Perfect place for our family for a weekend wedding in the area. Comfortable picturesque and very clean."
Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.

Historic 1817 Berkshire Farmhouse- Close to Everything!

10.0 out of 10, Exceptional, (1)
"A sweet little farm house perfect for a long weekend getaway. We love the lofty primary bed room and excellent mattress, exposed beams and well-supplied and modern kitchen. Great location between Lee and Lenox, made it easy to get all around the Berkshires. All the equipment and appliances m the house were clean and updated. Quiet neighborhood, lovely and large state forest right close by. "
Historic 1817 Berkshire Farmhouse- Close to Everything!

Farmhouse on Otis Pond

10.0 out of 10, Exceptional, (1)
"We had a wonderful time at the farmhouse. It is a charming old home. Our son loved being able to wake up and go fishing. The owner quickly responded to any questions. I loved sitting on the porch swing and listening to the birds."
Farmhouse on Otis Pond

18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC

10.0 out of 10, Exceptional, (1)
"We were happy to find such a large, comfortable home. The owner was very helpful. Lovely stay"
18th century 3-bedroom renovated farmhouse in peaceful Whately with WiFi, AC

NEW RENO - Chalet-style farm loft near Tanglewood

The price is AED 275
AED 624 total
includes taxes & fees
30 Dec - 31 Dec
NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Historic Loft w/views of the Berkshires

10.0 out of 10, Exceptional, (3)
"We were attending a weekend class. The bed was very comfortable and the apartment had everything we needed. The owner was very responsive. I would stay here again."
The price is AED 393
AED 753 total
includes taxes & fees
30 Dec - 31 Dec
NEW RENO - Historic Loft w/views of the Berkshires

Restored historic farmhouse on 25 private acres

10.0 out of 10, Exceptional, (1)
"Beautiful property, very well maintained and with good access to nearby towns and attractions. We enjoyed the swimming pond and sampled the garden produce. A lovely place to vacation."
Restored historic farmhouse on 25 private acres

Secluded 19th century Farmhouse with mountain views

10.0 out of 10, Exceptional, (1)
"We had a great time on our recent trip to Berkshires. It was due largely in part because of some excellent and charming accomodations at Jeff's family farmhouse. Our large group loved the farmhouse's layout, old world charm and beautiful property."
Secluded 19th century Farmhouse with mountain views

ONTARA....

ONTARA....

1789 Shaker Farmhouse in Berkshires/Hudson Valley

The price is AED 591
AED 1,557 total
includes taxes & fees
29 Dec - 30 Dec
1789 Shaker Farmhouse in Berkshires/Hudson Valley

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood

Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood

1800s Carriage house in Berkshires / Hudson Valley

The price is AED 312
AED 665 total
includes taxes & fees
7 Jan - 8 January 2025
1800s Carriage house in Berkshires / Hudson Valley
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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Other property types in Windsor

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 694
AED 762 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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.