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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Winchester

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

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

8.8 out of 10, Excellent, (47)
"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
Waterfront Cottage on Scenic Sportsman Pond
Exterior

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

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

10.0 out of 10, Exceptional, (29)
"The Host is very easy to contact and works well with our travelers."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
Exterior

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!
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

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 SAR 832
SAR 1,029 total
includes taxes & fees
18 Jun - 19 Jun
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Finnish Cabin with Sauna on Lake Monomonac
Exterior

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."
The price is SAR 709
SAR 1,108 total
includes taxes & fees
13 Jul - 14 Jul
Finnish Cabin with Sauna on Lake Monomonac
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Terrace/patio

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
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (20)
"This cute cottage served our family of 5 adults. It was clean and well decorated. Would definitely recommend. "
Cottage on Partridge Pond
Charming Jaffrey Cottage w/ Deck & Grill!
Fridge, microwave, stovetop, dishwasher

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (39)
"Great stay for family, nice gathering for grandparents and adult children."
Charming Jaffrey Cottage w/ Deck & Grill!
Charming Jaffrey Cottage w/ Deck & Grill!
Cottage (4 Bedrooms) | Interior

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Cavalier Cottage B&B
Room, Private Bathroom (Spencer) | Living area | 28-inch flat-screen TV with satellite channels, TV, DVD player

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
Cavalier Cottage B&B
Historic Home w/ Modern Updates on < 4 Acres
House (4 Bedrooms) | Interior

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
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Interior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

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

9.6 out of 10, Exceptional, (64)
"If you're looking to get away from it all then this is the place for you! Picturesque scenery. The nearby shops and markets were great, especially the farmers market. We would love to stay here again. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Hike & Swim On-site: Cozy Falls Brook Cabin
House (2 Bedrooms) | Interior

Hike & Swim On-site: Cozy Falls Brook Cabin

3.0 star property
10.0 out of 10, Exceptional, (2)
Hike & Swim On-site: Cozy Falls Brook Cabin
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
House (1 Bedroom) | Interior

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!
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior

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!
Grey Cabin with Sauna on Lake Monomonac
Property grounds

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 ."
The price is SAR 943
SAR 1,499 total
includes taxes & fees
17 Jun - 18 Jun
Grey Cabin with Sauna on Lake Monomonac
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Terrace/patio

Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

9.6 out of 10, Exceptional, (4)
"Lovely, relaxing setting, with beautiful views and steps away from the lake, with access to kayaks, canoes and paddleboards. The hosts were accessible, friendly and responsive. "
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
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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