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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Winchester

Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
10.0 out of 10, Exceptional, (2)
"Had a great time . Excellent communication Very clean .Would definitely stay there again. "
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Outdoor dining
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
8.6 out of 10, Excellent, (59)
"Great location and super cute"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
10.0 out of 10, Exceptional, (9)
"Beautiful property and great a host! My boys loved getting up early and fishing into the night! Perfect get away from the hustle and bustle of every day life. If you love nature this is a great place. Lots to explore! We had a GREAT also caught some good size BASS. Definitely will be back again. Thanks tons, The Gallant Family "
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Exterior
The Jelly Mill-A Peaceful River Retreat
The Jelly Mill-A Peaceful River Retreat
10.0 out of 10, Exceptional, (62)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
The Jelly Mill-A Peaceful River Retreat
Smart TV, fireplace, DVD player, ping pong
Beautiful Custom Built Timber Frame Home, Sleeps 11
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
Fridge, microwave, oven, stovetop
Bright three-level home with water views, jetted tub, firepit, and pool table
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
Microwave, oven, stovetop
Riverfront 2 Bedroom Unit 2
Riverfront 2 Bedroom Unit 2
9.8 out of 10, Exceptional, (25)
"Very pleasant stay."
Riverfront 2 Bedroom Unit 2
Fridge, microwave, oven, stovetop
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (25)
"great location"
The price is HK$739
HK$1,393 total
includes taxes & fees
3 Nov - 4 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!
Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
The price is HK$1,050
HK$1,969 total
includes taxes & fees
20 Oct - 21 Oct
Wellness Getaway with a Personal Sauna, and Private River Beach!
Fridge, microwave, oven, stovetop
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (61)
"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
Outdoor dining
Beautiful, private log cabin with huge, relaxing screened porch
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (41)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch
Property grounds
Family Friendly Hilltop House In Putney Vermont
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 HK$917
HK$1,907 total
includes taxes & fees
28 Oct - 29 Oct
Family Friendly Hilltop House In Putney Vermont
3 bedrooms, travel cot, free WiFi, bed sheets
Charming Waterfront Log Cabin
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (43)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Exterior
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
2.0 star property
10.0 out of 10, Exceptional, (24)
"The perfect cabin for a weekend getaway. The cabin had everything we needed and more!!! "
The price is HK$1,673
HK$2,753 total
includes taxes & fees
20 Oct - 21 Oct
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Interior
Cottage on Partridge Pond
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (25)
"Was a little nervous with the square footage but boy they have maximized every inch of this house. Lake was glorious, rooms were comfortable and all the extras were top notch. Already booked another stay for later this year. Such a perfect place for our family."
Cottage on Partridge Pond
Interior
Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (39)
"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 HK$903
HK$1,582 total
includes taxes & fees
19 Oct - 20 Oct
Lovely 2nd Floor Apartment
Smart TV, fireplace, table football, books
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
10.0 out of 10, Exceptional, (30)
"The house was so well stocked and very child friendly. So many personal touches that made us feel at home and comfortable. Would definitely stay again!"
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Exterior
Waterfront Cottage on Scenic Sportsman Pond
Waterfront Cottage on Scenic Sportsman Pond
9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Cozy Updated Log Cabin with Mountain Views close to Monadnock
9.4 out of 10, Exceptional, (26)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Fridge, microwave, oven, stovetop
Riverside Retreat – Cozy 2-Story Getaway!
Riverside Retreat – Cozy 2-Story Getaway!
9.8 out of 10, Exceptional, (32)
"This was perfect for two nights, two adult friends just looking for some quiet time away from kids. Property was clean and peaceful and had all of the basics. "
Riverside Retreat – Cozy 2-Story Getaway!
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

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

8/10 Good
"The room HVAC worked but is noisy. I don't mind because i like to sleep to white noise. Decent hotel. Not fancy at all. Seasonal prices were high compared to what i usually pay around the country. Vermont hotels seem to always be expensive Only bare essentials in room. Good tv channel selection."
Dan 2-night trip
Posted 23 hours ago
Travelodge by Wyndham Brattleboro VT

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Rhododendron State Park, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Winchester. Make sure you have time to check out the forests and waterfront during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Winchester?

Rhododendron State Park and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, Pisgah State Park and New England Sweetwater Farm & Distillery are other places worth a visit.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.