Holiday Rentals in Winchester

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Winchester

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

Beautiful Custom Built Timber Frame Home, Sleeps 11

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
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.

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.
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend
10.0 out of 10, Exceptional, (6)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

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 €560
includes taxes & fees
30 Nov - 1 Dec
FaLL Western Mass Getaway-Airhockey-Firepit
Terrace/patio
Old Deerfield Treasure!

Old Deerfield Treasure!

2.0 star property
Deerfield
The price is €447
includes taxes & fees
14 Dec - 15 Dec
Old Deerfield Treasure!
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

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 €179
includes taxes & fees
29 Nov - 30 Nov
Lovely 2nd Floor Apartment
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

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
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

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
Exterior
Beautiful Adirondack Cabin with Sauna on Lake Monomonac

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
Rindge
10.0 out of 10, Exceptional, (24)
"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"
United States
Leigh C.
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
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
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is €225
includes taxes & fees
1 Dec - 2 Dec
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.

Peterborough
9.8 out of 10, Exceptional, (28)
"I had a great stay at Mary Anne and Ben’s place in Peterborough. The apartment was clean and comfortable, and the location cannot be beat."
United States
Joseph K.
The price is €133
includes taxes & fees
2 Dec - 3 Dec
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Rindge
10.0 out of 10, Exceptional, (22)
"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."
United States
Nicole B.
The price is €321
includes taxes & fees
1 Dec - 2 Dec
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

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
Exterior
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

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
Interior
Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster
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."
United States
Jessica K.
Cottage on Partridge Pond
Fridge, microwave, oven, stovetop
Riverside Retreat – Cozy 2-Story Getaway!

Riverside Retreat – Cozy 2-Story Getaway!

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!
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

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
Exterior
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

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
Smart TV, fireplace, DVD player, books
This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!

This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!

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!
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is €248
includes taxes & fees
30 Nov - 1 Dec
Family Friendly Hilltop House In Putney Vermont
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

Econo Lodge Brattleboro

Econo Lodge Brattleboro

6/10 Okay
"Room had good lighting,room was nice and warm had hot water. walls could use some fresh paint, ceiling was very dusty, bathroom had smell of stagnant water. Tub had chipped enamel and mold around bottem of tub by floor. Outer sink was slow to drain. Beds were horrible, very old and saggy. Sheets smelled of detergent and made our skin itch. "
Cheryl Eng 1-night trip
Posted 2 days ago
Econo Lodge Brattleboro

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €133 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.