Winchester Holiday Rentals

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Check prices for these dates

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Winchester

Smart TV, fireplace, DVD player, ping pong
Beautiful Custom Built Timber Frame Home, Sleeps 11

Holiday Home in Wilmington

10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Interior
Lovely 2nd Floor Apartment

Holiday Home in Greenfield

10.0 out of 10, Exceptional, (44)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is HK$904
HK$1,575 total
includes taxes & fees
3 Dec - 4 Dec
Lovely 2nd Floor Apartment
Outdoor dining
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Mobile Home in Fitzwilliam

10.0 out of 10, Exceptional, (10)
"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"
United States
Seth K.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

Holiday Home in Colrain

9.8 out of 10, Exceptional, (38)
"Great place and convenient to get to and from Berkshire East."
United States
Jeffrey B.
The price is HK$2,141
HK$4,905 total
includes taxes & fees
2 Dec - 3 Dec
FaLL Western Mass Getaway-Airhockey-Firepit
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Holiday Home in Townshend

10.0 out of 10, Exceptional, (6)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Fridge, microwave, oven, stovetop
Riverside Retreat – Cozy 2-Story Getaway!

Apartment in Millers Falls

9.8 out of 10, Exceptional, (35)
"Place was very nice, there were plenty of useful items in the house, everything was thought of. I would recommend this place to others."
United States
Michael A.
Riverside Retreat – Cozy 2-Story Getaway!
Outdoor dining
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in Wilmington

8.6 out of 10, Excellent, (63)
"Great location and super cute"
United States
Jeff S.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Fridge, microwave, oven, stovetop
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Holiday Home in Townshend

10.0 out of 10, Exceptional, (62)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Exterior
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Holiday Home in Peterborough

10.0 out of 10, Exceptional, (71)
"The property was absolutely perfect. House was even better than the pictures with so much space to spread out with a large family. It is apparent that the owners take great pride in making it nice. Everything was spotless! The surrounding grounds were also beautiful."
United States
Kathleen S.
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,051
HK$1,979 total
includes taxes & fees
7 Dec - 8 Dec
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cabin in Townshend

10.0 out of 10, Exceptional, (59)
"THE perfect place to stay for a getaway weekend (or longer!). Courtney was so responsive and helpful. Cannot recommend this place enough. :)"
United States
Patricia Emogene M.
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Smart TV, fireplace, table football, books
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Holiday Home in Whitingham

10.0 out of 10, Exceptional, (31)
"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!"
United States
Brittany M.
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Smart TV, fireplace, DVD player, books
This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!

Cabin in Halifax

9.8 out of 10, Exceptional, (120)
"Great place to stay with friends and family. Will be visiting again!"
United States
Adam K.
This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Cabin in Fitzwilliam

9.6 out of 10, Exceptional, (28)
"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. "
United States
Jennifer
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Fridge, microwave, oven, stovetop
Nestled on the edge of the woods near Mount Monadnock

Holiday Home in Jaffrey

9.6 out of 10, Exceptional, (7)
"Very nice stay at railtrail retreat."
United States
David O.
Nestled on the edge of the woods near Mount Monadnock
Exterior
The Jelly Mill-A Peaceful River Retreat

Holiday Home in Guilford

10.0 out of 10, Exceptional, (64)
"Beautiful rural location next to the Green River. A peaceful relaxing place to stay. We would love to stay here again "
United States
Georgene M.
The Jelly Mill-A Peaceful River Retreat
Exterior
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

Cabin in Rindge

9.8 out of 10, Exceptional, (51)
"Ryan’s property is beautiful and peaceful. Its exactly what I would describe as a perfect summer getaway."
United States
Elizabeth S.
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Holiday Home in Walpole

10.0 out of 10, Exceptional, (50)
"Worked out perfectly for us!"
United States
Andrew P.
The price is HK$1,962
HK$4,308 total
includes taxes & fees
2 Dec - 3 Dec
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Exterior
Waterfront Cottage on Scenic Sportsman Pond

Cottage in Fitzwilliam

9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
United States
Cathy M.
Waterfront Cottage on Scenic Sportsman Pond
Property grounds
Beautiful Townhouse In Turners Falls!

Apartment in Turners Falls

9.8 out of 10, Exceptional, (142)
"Very comfortable place for my wife and I. Location is ideal for exploring the Berkshires and points north and south. We’ll likely be back for another stay."
United States
Mark E.
Beautiful Townhouse In Turners Falls!
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"The Victrola and records in the room were awesome!"
Derek 1-night trip
Posted 2 days ago
Latchis Hotel

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?

Beautiful Custom Built Timber Frame Home, Sleeps 11: This holiday home rental outside of Winchester is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Winchester?

Birch Point 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.