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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 48 Cottages in Winchester with updated reviews, rates, and availability.

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
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.
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 AED 752
AED 911 total
includes taxes & fees
15 Apr - 16 Apr
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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
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)
"Stayed twice would stay again"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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 AED 804
AED 1,200 total
includes taxes & fees
15 Apr - 16 Apr
Finnish Cabin with Sauna on Lake Monomonac
Grey Cabin with Sauna on Lake Monomonac
Property grounds

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
6.0 out of 10, (2)
"This was our 2nd stay with the host. Everything was perfect and relaxing. "
The price is AED 841
AED 1,367 total
includes taxes & fees
15 Apr - 16 Apr
Grey Cabin with Sauna on Lake Monomonac
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)
"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
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (18)
"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
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!
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!
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!
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
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!
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!
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
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.
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

GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat
Riverfront 2 Bedroom Unit 2
Property grounds

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
Riverfront 2 Bedroom Unit 2
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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