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Browse Select Winchester Holiday Homes

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is £317
includes taxes & fees
28 Aug - 29 Aug
Downtown Hot Tub Escape

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (34)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is £154
includes taxes & fees
28 Aug - 29 Aug
Lovely 2nd Floor Apartment

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (8)
"We had a wonderful stay here over three nights in mid-April. We loved the style and personal touches of the property, and our dog loved how dog friendly it was and especially loved being able to prance around the beach and pull sticks out of the lake. Our visit was fantastic, and we’d happily come back sometime — well worth it!"
Story Book Lake Front Chateau with Private Beach!

Quiet private pond getaway

9.4 out of 10, Exceptional, (14)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (106)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (57)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Cozy Lakefront Cottage

9.8 out of 10, Exceptional, (16)
"Me and my children had an amazing time exploring the lake."
Cozy Lakefront Cottage

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

10.0 out of 10, Exceptional, (67)
"We enjoyed our stay at this beautiful spacious property. The owner was very helpful and responsive. I’d definitely recommend staying here if you are in the area."
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 8

10.0 out of 10, Exceptional, (47)
"A charming updated farmhouse. Lots of sitting and dining areas.... lovely stay."
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 8

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is £259
includes taxes & fees
13 Sept - 14 Sept
Family Friendly Hilltop House In Putney Vermont

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (41)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

Mountain view home with expansive deck, pellet stove, hot tub and outdoor shower

10.0 out of 10, Exceptional, (1)
"This home is beautiful inside and out! I highly recommend it to groups of people. There is so much space to gather and room for alone time. "
Mountain view home with expansive deck, pellet stove, hot tub and outdoor shower

Cozy cottage tucked away in the woods

9.8 out of 10, Exceptional, (45)
"Nice and comfy - loved the decor and the property."
Cozy cottage tucked away in the woods

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (16)
"We had a lovely stay our 2nd time at this location and we will definitely come back. Kevin designed a thoughtful 2 bedroom with lovely furniture and art located in Shelburne Falls which is such a beautiful area."
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (17)
"Very clean, well equipped and thoughtfuly supplied. An extra bonus were the great assortment of books, games, movies, and puzzles available. A great deal of experience and generosity went into choices made, and it was much appreciated. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Lakes and Hiking Summertime - Spacious 4-bedroom Pet Friendly Home

10.0 out of 10, Exceptional, (5)
"We had a great experience at Erika’s place. The house was great. Spacious & cozy at the same time. Plenty of amenities to keep the kids entertained from the theater in the basement to card games, fussball, darts, backyard, and firepit,for roasting marshmallows. We hiked at Molly Stark, went to the reservoir, & skied at Mt. Snow all in under 20 min away. We had a good time, it was a perfect getaway for our spring break. "
Lakes and Hiking Summertime - Spacious 4-bedroom Pet Friendly Home

Rustic, dog-friendly escape with private pool, sweeping views, & W/D

9.2 out of 10, Wonderful, (17)
"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"
Rustic, dog-friendly escape with private pool, sweeping views, & W/D

1770 House - An end of a dirt road hideaway where you can relax and unwind.

10.0 out of 10, Exceptional, (3)
"Absolutely beautiful property. Our three kids enjoyed the pool/jacuzzi and the expansive outdoor area daily. Ed was very accommodating and communicate. "
1770 House - An end of a dirt road hideaway where you can relax and unwind.

Four Season Woodsy Retreat with Private Pool. Skiing, Hiking, Kayaking

Four Season Woodsy Retreat with Private Pool. Skiing, Hiking, Kayaking
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 Holiday Homes information

Number of reviews
337
Accommodation
126 Holiday Homes
Lowest Price
£154
Highest Price
£317