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Vacation Homes in Winchester

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"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 SAR 435
SAR 759 total
includes taxes & fees
19 Sep - 20 Sep
Lovely 2nd Floor Apartment

Bright three-level home with water views, jetted tub, firepit, and pool table

8.6 out of 10, Excellent, (34)
"Quite secluded clean comfy cabin We enjoyed it very much. Very close to the things we wanted to do."
Bright three-level home with water views, jetted tub, firepit, and pool table

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (20)
"Nice house in a nice location. "
The price is SAR 861
SAR 1,524 total
includes taxes & fees
22 Sep - 23 Sep
Downtown Hot Tub Escape

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

10.0 out of 10, Exceptional, (59)
"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

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 SAR 731
SAR 1,273 total
includes taxes & fees
19 Sep - 20 Sep
Family Friendly Hilltop House In Putney Vermont

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (39)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch

Quiet private pond getaway

9.4 out of 10, Exceptional, (15)
"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

A vacation destination in Southern Vermont

10.0 out of 10, Exceptional, (71)
"Super comfortable cabin in a great location."
A vacation destination in Southern Vermont

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

FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit

9.8 out of 10, Exceptional, (36)
"Great place and convenient to get to and from Berkshire East."
The price is SAR 1,032
SAR 2,363 total
includes taxes & fees
22 Sep - 23 Sep
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit

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

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

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.

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

Beautiful Lakefront home - perfect getaway for every season!

10.0 out of 10, Exceptional, (5)
"We had an incredible stay at the lake house. Michelle and Patrick were absolutely wonderful to work with and very responsive throughout our stay. The home is beautiful. Waking up to the lake each morning was such a treat. We definitely hope to visit again!"
Beautiful Lakefront home - perfect getaway for every season!

Inviting mountain view home with game room, balcony & W/D

9.0 out of 10, Wonderful, (9)
"The location was perfect, no traffic and nice walking area. The house has such a wonderful lay out with 2 living/sitting rooms so all family members could enjoy their own space then enjoy nice family meals on the big dining table together."
Inviting mountain view home with game room, balcony & W/D

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

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

The Dover Hideaway | Hot Tub & Close to Mt. Snow

10.0 out of 10, Exceptional, (1)
"Beautiful property. Very secluded but close to a lot of fun stuff."
The Dover Hideaway | Hot Tub & Close to Mt. Snow
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