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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare 41 Cottages in Winchester with updated reviews, rates, and availability.

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, (46)
"The cabin is cozy and sweet- we have a dog and small family and wanted to ski at Mt Snow. Cabin is short 20 minute drive to ski. Super cute town of Wilmington just a few minutes away. Go to Dots or Alpen Glow! Shaws grocery 2 minutes away. House has Pottery Barn vibes. Decent sized kitchen sitting and dining area. 2Bedroom 2 bath. This is not a house for a large crew but for a family getaway it was perfect. Street is quiet and residential. Neighbors seem really friendly. We would love to come...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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 831
SAR 1,028 total
includes taxes & fees
7 Mar - 8 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Finnish cottage with Sauna on Lake Monomonac
Exterior

Finnish cottage 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 559
SAR 912 total
includes taxes & fees
18 Mar - 19 Mar
Finnish cottage with Sauna on Lake Monomonac
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 Modern Cottage with Sauna on Lake Monomonac
Property grounds

Beautiful Modern Cottage with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was our 2nd stay with the host. Everything was perfect and relaxing. "
The price is SAR 671
SAR 1,168 total
includes taxes & fees
9 Mar - 10 Mar
Beautiful Modern Cottage with Sauna on Lake Monomonac
Waterfront Cottage on Scenic Sportsman Pond
Exterior

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (41)
"Sportsman's Pond and Blueberry Cottage provided the ideal location for disconnecting from the noise and busyness of every day life. The pond was beautifully serene, without outboard motors, jet skis, etc. The fall colors were gorgeous. The hosts provided every sort of watercraft one might want. I kayaked everyday exploring the shoreline and watching for birds. The cottage was well equipped, the bed was comfortable and an assortment of chairs and couches were available for lounging, viewing the...
Waterfront Cottage on Scenic Sportsman Pond
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (17)
"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)
"Stayed four nights. Perfect weather and the foliage was fabulous.The cottage was ideal for us. Tastefully decorated and everything labeled. Wish we lived closer so we could go again in other seasons."
Charming Jaffrey Cottage w/ Deck & Grill!
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, (16)
"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
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, (63)
"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
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!
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)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Hike & Swim On-site: Cozy Falls Brook Cabin
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)
"This lake house has it all. Views, nature, wildlife and so many things to do. Kayak, paddleboard, fishing, boating and so much more! Highly recommend! The host is top notch! "
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
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!
Jacksonville Cabin w/ Wraparound Deck & Views
House (3 Bedrooms) | Interior

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Charming Putney Home: Porch, Grill & Hiking Trails
House (4 Bedrooms) | Interior

Charming Putney Home: Porch, Grill & Hiking Trails

3.0 star property
Charming Putney Home: Porch, Grill & Hiking Trails
Cozy Tiny House on Main Street. Fully Renovated.
Exterior

Cozy Tiny House on Main Street. Fully Renovated.

10.0 out of 10, Exceptional, (4)
"I was in Dublin visiting my daughter who goes to high school here and it was the perfect place for me to stay and she stayed with me two nights. The owner thought of everything you would need. It was super clean and everything looked brand new. Really well decorated. The owner was super helpful and I’m sure I’ll be back before my girl graduates. Highly recommend!"
Cozy Tiny House on Main Street. Fully Renovated.
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!
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!
Cottage Lake Nubanusit
Fridge, microwave, oven, stovetop

Cottage Lake Nubanusit

10.0 out of 10, Exceptional, (2)
"A lovely patina from years of caring use, authentic, genuine, simple and very comfortable. Well equipped, everything works. Screen porch is perfect. Dock and shoreline easy and very pretty, perfect for kayaks/canoes. We look forward to a future stay!"
Cottage Lake Nubanusit
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

Secluded Lakefront Vacation Home
Smart TV, fireplace, books, printers

Secluded Lakefront Vacation Home

9.8 out of 10, Exceptional, (69)
"Once again I was placed into a state of memories starting from childhood when I used to swim in Lake Sunshine(now lake Contoocook! The scenery is mesmerizing and I love staring at the trees and lake which takes me back to days of freedom and wonderment. The sunrises are spectacular and make me begin a new day with energy and hope for this unsettled world."
Secluded Lakefront Vacation Home
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, (46)
"The cabin is cozy and sweet- we have a dog and small family and wanted to ski at Mt Snow. Cabin is short 20 minute drive to ski. Super cute town of Wilmington just a few minutes away. Go to Dots or Alpen Glow! Shaws grocery 2 minutes away. House has Pottery Barn vibes. Decent sized kitchen sitting and dining area. 2Bedroom 2 bath. This is not a house for a large crew but for a family getaway it was perfect. Street is quiet and residential. Neighbors seem really friendly. We would love to come...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cozy 2-bedroom Unit with private backyard
Fridge, microwave, oven, stovetop

Cozy 2-bedroom Unit with private backyard

10.0 out of 10, Exceptional, (21)
"Small but very clean and had everything we needed for our stay "
Cozy 2-bedroom Unit with private backyard
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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