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Check prices for these dates

Next weekend
19 Sept - 21 Sept
In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Featured Cottages in Winchester

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

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

8.6 out of 10, Excellent, (57)
"Stayed twice would stay again"
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, (43)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond
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)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
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, (66)
"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
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Outdoor dining

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

9.8 out of 10, Exceptional, (7)
"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. "
The price is AU$750
includes taxes & fees
5 Oct - 6 Oct
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Exterior

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

10.0 out of 10, Exceptional, (35)
"The Host is very easy to contact and works well with our travelers."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Quaint Massachusetts Home w/ Yard & Grill!
House (2 Bedrooms) | Interior

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Quaint Massachusetts Home w/ Yard & Grill!
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!
Exterior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
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!
Cottage on Partridge Pond
Interior

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (23)
"Nicely appointed with pretty view. "
Cottage on Partridge Pond
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
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!
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 AU$515
includes taxes & fees
9 Sept - 10 Sept
Finnish Cabin with Sauna on Lake Monomonac
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, (8)
"Short time we had there but everything was great would love to stay again for personal trip and see more of the farm "
The price is AU$486
includes taxes & fees
10 Sept - 11 Sept
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
House (2 Bedrooms) | Interior

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Exterior

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!
Cavalier Cottage B&B
Exterior

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
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
Grey Cabin with Sauna on Lake Monomonac
Exterior

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
7.6 out of 10, Good, (4)
"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"
The price is AU$582
includes taxes & fees
9 Sept - 10 Sept
Grey Cabin with Sauna on Lake Monomonac
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
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

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
Accommodation
52 Cottages
Lowest Price
AU$486
Highest Price
AU$750

Frequently asked questions

What is there to do in Winchester near my cottage?
Whatever you love to do, Winchester has a whole lot to keep you on the move. Pisgah State Park, Asbury United Methodist Church and Little Monadnock Mountain are on most visitors' sightseeing itineraries. Don't head home without exploring Birch Point, Madame Sherri Forest and Thomas Aquinas College either. With Expedia's hotel deals in Winchester, you'll be able to discover even more fantastic attractions like these with the money you save.