Winchester Holiday Rentals

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (28)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is AU$630
includes taxes & fees
30 Sept - 1 Oct
The Blue Elm - A Historic Berkshire Cottage

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (24)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AU$1,062
includes taxes & fees
22 Sept - 23 Sept
Guesthouse Cabin vacation rentals in Berkshire County

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (81)
"Wonderful time, beautiful lakeside view"
Lakefront Fall Foliage in New England Just 2 Hours From NYC

LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

10.0 out of 10, Exceptional, (15)
"Everything we hoped for and more. Throwback cabin, quaint, comfortable, character. "
LAKE FRONT ISLAND HIDE-AWAY WITH BOAT DOCK

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is AU$1,782
includes taxes & fees
23 Sept - 24 Sept
Whispering Estate Guest House - A Romantic Countryside Getaway

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.2 out of 10, Wonderful, (7)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
The price is AU$879
includes taxes & fees
22 Sept - 23 Sept
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (69)
"We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!"
Bluebird Valley Farmhouse

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (20)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (60)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is AU$682
includes taxes & fees
22 Sept - 23 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"we couldn't ask for a better place. It had all the conveniences we like. The host did a great job here."
The Goshen Glass Chalet

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is AU$547
includes taxes & fees
21 Sept - 22 Sept
Big farmhouse in the foothills of the Berkshires

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

10.0 out of 10, Exceptional, (1)
"Clean and quiet location, great place for a relaxing stay."
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

Linny's Lakeview Cottage - Cozy, fun & updated

10.0 out of 10, Exceptional, (62)
"Very great location, close to my family. Great spot!!"
Linny's Lakeview Cottage - Cozy, fun & updated
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

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, 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 favourite 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 depend 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 AU$547 per night. Entering your travel dates in the search wizard might find you 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

Are there holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Laurel Lanes, or you can select a more secluded option if you're looking for a relaxing stay.

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

Lakefront Fall Foliage in New England Just 2 Hours From NYC: 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals will I find in Winchester?

Expedia has 7 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Highland Lake and Walker Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Burr Pond State Park and Platt Hill State Park 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 such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family getaway.