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Cottages in Winchester

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

8.8 out of 10, Excellent, (50)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (41)
"Great stay for family, nice gathering for grandparents and adult children."
Charming Jaffrey Cottage w/ Deck & Grill!

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

10.0 out of 10, Exceptional, (17)
"It was a great place for what I needed. I was working in the area and it was a great quiet location, with nice scenery. The place was clean and spacious, with plenty of space to cook. I would definitely stay here again."
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (41)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!

Finnish Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (10)
"This was a very nice cozy cottage, with a nice view of the water. The host was friendly and accommodating. We look forward to staying again."
Finnish Cabin with Sauna on Lake Monomonac

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

10.0 out of 10, Exceptional, (30)
"The Host is very easy to contact and works well with our travelers."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (21)
"This is the second time we have rented the cottage. It is such a delightful place to stay and the hosts provide such lovely amenities, that I would say it's one of the best rental experiences we've encountered. "
Cottage on Partridge Pond

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

10.0 out of 10, Exceptional, (13)
"This house was great! It provided an amazing place to stay for our son’s wedding! Would rent again! Jacuzzi was a nice addition!"
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
Cavalier Cottage B&B

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is AED 814
AED 999 total
includes taxes & fees
21 Jul - 22 Jul
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
7.4 out of 10, Good, (3)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
Grey Cabin with Sauna on Lake Monomonac

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (64)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

Hike & Swim On-site: Cozy Falls Brook Cabin

3.0 star property
10.0 out of 10, Exceptional, (2)
The price is AED 536
AED 1,311 total
includes taxes & fees
26 Jul - 27 Jul
Hike & Swim On-site: Cozy Falls Brook Cabin

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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 Winchester Hotel Reviews

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