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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 13 Farmstay in Winchester with updated reviews, rates, and availability.

Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10
Gorgeous post and beam colonial.

Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10

10.0 out of 10, Exceptional, (2)
"We had a wonderful stay in this older charming house. It was the perfect size for our family get together and the hosts were so great. Will stay here again without a doubt!!"
Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10
Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow
A stunning kitchen to gather with family and friends

Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow

Luxury Farm Stay - Bonds Corner Bungalow - Wolf Pine Hollow
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
Exterior

Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC

2.0 star property
The price is AED 826
AED 1,444 total
includes taxes & fees
4 Feb - 5 Feb
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
Stunning views on 545 acres at end of dirt road
View into Vermont

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
The Robin’s Nest - Beautiful New Hampshire Country
Interior

The Robin’s Nest - Beautiful New Hampshire Country

7.4 out of 10, Good, (3)
"We definitely enjoyed our stay. Beautiful place and the host was very responsive and accommodating "
The Robin’s Nest - Beautiful New Hampshire Country
Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow
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Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow

10.0 out of 10, Exceptional, (1)
"Such a fun house for our girls’ weekend. We nicknamed it the tea party house. Artfully deco-rated….flowers everywhere. Even a candy room!!! Very clean, very comfortable and lots of perks. Loved it. And we loved the tulip tour!"
Luxury Farm Stay at Glenrose Manor - Wolf Pine Hollow
Your own private farmhouse on spectacular farm, quiet and peaceful. S. NH/VT
Exterior

Your own private farmhouse on spectacular farm, quiet and peaceful. S. NH/VT

10.0 out of 10, Exceptional, (34)
"My husband and I stayed with my parents and in-laws for one night in December. Everything was so wonderful! Excellent communication from the host, very clean, and a beautiful kitchen to make a meal in! Highly recommend!"
The price is AED 1,117
AED 1,347 total
includes taxes & fees
4 Feb - 5 Feb
Your own private farmhouse on spectacular farm, quiet and peaceful. S. NH/VT
Cozy Farmhouse & Ski Just 27 Mins from Wachusett!
Sport court

Cozy Farmhouse & Ski Just 27 Mins from Wachusett!

10.0 out of 10, Exceptional, (1)
"We wanted a quiet weekend away, and that is what we had. We enjoyed walks, going to Red Apple Farm, a hike around the pond at Dunn State Park, and just relaxing at the house. It was very nice."
Cozy Farmhouse & Ski Just 27 Mins from Wachusett!
3 Bedroom Cottage Rental with beautiful farm views
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3 Bedroom Cottage Rental with beautiful farm views

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay at the cozy Kilburn cottage, originally a sheep barn turned into workers housing in the 40s. We are very familiar with this beautiful area so knew where we were going and the setting. The attached ‘cottage’ at the Inns rear wing is charming and was just what we needed for visiting family nearby. It had all we needed for the 3 adults staying over and a family visitor for dinner. Loved the farm kittens and the views. The nature trail wasn’t open at the time of our visit as...
The price is AED 896
AED 1,079 total
includes taxes & fees
4 Feb - 5 Feb
3 Bedroom Cottage Rental with beautiful farm views
Luxury Farm Stay at The Lodge at Wolf Pine Hollow
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Luxury Farm Stay at The Lodge at Wolf Pine Hollow

10.0 out of 10, Exceptional, (3)
"We just loved our stay in this beautiful home. It was stocked with everything you’d need, incredibly clean. I wholeheartedly recommend this home. "
Luxury Farm Stay at The Lodge at Wolf Pine Hollow
Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow
A romantic nook for special moments.

Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow

10.0 out of 10, Exceptional, (1)
"Cute, cozy, well appointed, perfect for couple or family with small children. Lovely setting! "
Luxury Farm Stay-The Cottage at Glenrose - Wolf Pine Hollow
200 y.o. Farmhouse secluded in its own valley with 2 ponds
Exterior

200 y.o. Farmhouse secluded in its own valley with 2 ponds

10.0 out of 10, Exceptional, (1)
"Beautiful peaceful property for family to gather!"
200 y.o. Farmhouse secluded in its own valley with 2 ponds
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 Winchester

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Winter wonderland!

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (112)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

6.8 out of 10, (13)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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.