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

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 - 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
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 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, (32)
"The farmhouse was perfect for our weekend stay. Comfortable, clean and beautiful. Tessa made sure we had everything we needed. The farm cats were an added bonus. Thank you! "
The price is SAR 1,141
SAR 1,385 total
includes taxes & fees
7 Dec - 8 Dec
Your own private farmhouse on spectacular farm, quiet and peaceful. S. NH/VT
Spectacular farm views from family/couples cottage, Walpole NH, 3 mi to VT.
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Spectacular farm views from family/couples cottage, Walpole NH, 3 mi to VT.

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 SAR 916
SAR 1,122 total
includes taxes & fees
27 Nov - 28 Nov
Spectacular farm views from family/couples cottage, Walpole NH, 3 mi to VT.
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-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
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 SAR 845
SAR 1,306 total
includes taxes & fees
7 Dec - 8 Dec
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC
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!
Farm Stand Lodge
Exterior

Farm Stand Lodge

Farm Stand Lodge
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

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

9.0 out of 10, Wonderful, (42)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Living area

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (48)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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.