Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
East Granby
8.6 out of 10, Excellent, (4 reviews)
"Relaxing stay"
United States
Kim M.
The price is AU$765
includes taxes & fees
27 Mar - 28 Mar
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (18 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is AU$259
includes taxes & fees
5 Apr - 6 Apr
Peaceful Meadow Retreat

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (144 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AU$512
includes taxes & fees
27 Mar - 28 Mar
Big farmhouse in the foothills of the Berkshires

River Overlook - Check the view from your deck!

River Overlook - Check the view from your deck!
Collinsville
10.0 out of 10, Exceptional, (23 reviews)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is AU$412
includes taxes & fees
29 Mar - 30 Mar
River Overlook - Check the view from your deck!

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
The price is AU$540
includes taxes & fees
1 Apr - 2 Apr
Art House 3 Beds Close to Warner Theater

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is AU$561
includes taxes & fees
27 Mar - 28 Mar
Litchfield Retreat, Wineries, Foliage & Skiing

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is AU$991
includes taxes & fees
29 Mar - 30 Mar
Guesthouse Cabin vacation rentals in Berkshire County

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is AU$995
includes taxes & fees
29 Mar - 30 Mar
CT Gate House Goshen CT, Gate House Goshen CT

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
10.0 out of 10, Exceptional, (5 reviews)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
The price is AU$1,003
includes taxes & fees
29 Mar - 30 Mar
Stylish Townhome | Perfect for Family Gatherings & Events

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is AU$494
includes taxes & fees
29 Mar - 30 Mar
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is AU$449
includes taxes & fees
31 Mar - 1 Apr
Dugway Hideaway Walking Distance to Lime Rock Park

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"The place was absolutely spotless and magnificent in every way. Highly recommended."
United States
Robert A.
The price is AU$535
includes taxes & fees
27 Mar - 28 Mar
The Jefferson Guest House, Spacious, Special Views

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (63 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AU$730
includes taxes & fees
21 Apr - 22 Apr
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is AU$565
includes taxes & fees
29 Mar - 30 Mar
Cozy Modern Farmhouse Private Apt - 3 Beds

3-Bedroom Cabin Getaway With Rustic Charm

3-Bedroom Cabin Getaway With Rustic Charm
Cornwall
8.4 out of 10, Very good, (6 reviews)
"Absolutely beautiful cottage exactly as pictured inside and out. "
United States
Michaela C.
The price is AU$878
includes taxes & fees
1 Apr - 2 Apr
3-Bedroom Cabin Getaway With Rustic Charm

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is AU$390
includes taxes & fees
8 Apr - 9 Apr
The Historic Hideaway

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$703
includes taxes & fees
29 Mar - 30 Mar
Cheerful 3-bedroom cottage with woodstove

Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
New Preston
The price is AU$739
includes taxes & fees
15 Apr - 16 Apr
Dainty New Preston Cottage w/ Dock & Lake Views!

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield
Bloomfield
9.0 out of 10, Wonderful, (6 reviews)
"I had a great time and I felt very welcome"
United States
Avis b.
The price is AU$1,049
includes taxes & fees
29 Mar - 30 Mar
Spacious 5-bedroom townhome with WiFi and AC in charming Bloomfield

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$793
includes taxes & fees
30 Mar - 31 Mar
Treetop Hideaway in Tyringham
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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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$512 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?

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!: This holiday home rental outside of Winchester offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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, Platt Hill State Park and American Mural Project 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.