Winchester Holiday Rentals from €283: Search Short-Term Rentals

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Holiday Rentals in Winchester

"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"

includes taxes & fees

27 Jul - 28 Jul

"We had a nice stay while visiting our son at AOF. There were a couple of small issues which the owner remedied IMMEDIATELY. Things happen in life which are unforeseen, we appreciated the owner jumping on the issues quickly."

includes taxes & fees

28 Jul - 29 Jul

includes taxes & fees

20 Jul - 21 Jul

includes taxes & fees

20 Jul - 21 Jul

1 bedroom, desk, iron/ironing board, WiFi

"The lighting is warm and inviting as you step up the stairs into a large open concept room. Every detail is beyond modern from the giant marble counter equipped with the comfiest and largest leather barstools, to the kitchen whose colors and appliances are so beautifully designed; cabinets stocked with every item you need to cook a homemade meal.The king size bed was like a cloud, swallowing us in the fluffiest duvets and sheets, comfortable pillows, making it an easy switch to use the TV in the...

includes taxes & fees

20 Jul - 21 Jul

"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "

includes taxes & fees

20 Jul - 21 Jul

"My friends and stayed for a night. The house is nice and the owners is very communicative. "

includes taxes & fees

23 Jul - 24 Jul

includes taxes & fees

23 Jul - 24 Jul

"We had a great time and I would highly recommend for your next stay. Very clean and had everything to make your vacation enjoyable."

includes taxes & fees

21 Jul - 22 Jul

"The property was centrally located for skiing, and was a comfortable stay."

includes taxes & fees

22 Jul - 23 Jul

"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."

includes taxes & fees

27 Jul - 28 Jul

"We enjoyed our trip and the house was perfect for us, 3 boys and their father. "

includes taxes & fees

7 Aug - 8 Aug

"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."

includes taxes & fees

14 Aug - 15 Aug

"Property as advertised & convenient - nice location. Great communication; appreciate the hospitality! "

includes taxes & fees

10 Aug - 11 Aug

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Top Winchester Hotel Reviews

The Farmington Inn & Suites

10/10 Excellent

"Visiting friends in Farmington one year after moving away. The Farmington Inn was the perfect spot! Centrally located and walkable to restaurants and shopping. While the property isn’t brand new, it makes up for it in personal service, delightful amenities like wine and cheese in the lobby in the evening! Coffee available all day long! Very nice complimentary breakfast in a lovely setting! "

Simsbury 1820 House

10/10 Excellent

"We have stayed here several times over the last few years. We were always traveling by bicycle so we appreciate the restaurant choices nearby. The staff were very helpful with our bikes and allowing us to put them inside in Inn. The room was lovely with really nice touches. We received free water bottles and there is a refrigerator. Coffee and tea are always available in the breakfast room. I loved the comfy chairs in the room and the extra sink. The note pad and pen were a nice touch. Breakfast was much improved from the last time we stayed there. Many more options including fruit and yogurt, cold cereal, microwaveable breakfast sandwiches, and a nice selection of muffins, bagels, and breads. Note that if you have trouble climbing stairs, you need to request the first floor as there is no elevator. "

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 €283 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

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?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Winchester is located in a rural location, 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. You can relax into your holiday with a 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 Rowley Fields 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.

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Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Home in the Woods

Old Avon Village

CT Gate House Goshen CT, Gate House Goshen CT

This is Room sharing property we only listed the master bedroom and bathroom

The Jefferson Guest House, Spacious, Special Views

Private Room/Sunny/Clean/Peace/SelfCheckIn

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Tranquil Litchfield Connecticut Retreat".

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

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

Cheerful 3-bedroom cottage with woodstove

Charming 3-bedroom Modern cottage with lakeside views

Big farmhouse in the foothills of the Berkshires

Fave Cape Cod Style Home Retreat: with Main-Level Bedroom bordering Farmington

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

Premium 3-Story Townhome | Perfect for Large Groups

Top Winchester Hotel Reviews

The Farmington Inn & Suites

Avon Old Farms Hotel

Blackberry River Inn

Simsbury 1820 House

Home2 Suites by Hilton Bristol

Delamar West Hartford

The Abner Hotel

Homewood Suites by Hilton Hartford-Farmington

Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Frequently asked questions