Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
2.0 star property
The price is NZ$688
includes taxes & fees
4 Jan - 5 Jan
The Birdsong Apt. | Game Room & Fire Pit
9.6 out of 10, Exceptional, (4)
"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 NZ$600
includes taxes & fees
4 Jan - 5 Jan
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is NZ$425
includes taxes & fees
9 Jan - 10 Jan
The Historic Hideaway

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (16)
"Beautiful property comfy, cozy and clean little cottage."
United States
Denise T.
The price is NZ$320
includes taxes & fees
6 Jan - 7 Jan
Peaceful Meadow Retreat
10.0 out of 10, Exceptional, (4)
"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 NZ$701
includes taxes & fees
4 Jan - 5 Jan
Cozy Modern Farmhouse Private Apt - 3 Beds
2.5 star property
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is NZ$1,111
includes taxes & fees
18 Jan - 19 Jan
CT Gate House Goshen CT, Gate House Goshen CT
The price is NZ$217
includes taxes & fees
5 Jan - 6 Jan
Charming 1-bedroom in welcoming West Hartford with WiFi, AC

Holiday Home in Avon

Sun Filled Lake House Living
2.0 star property
6.0 out of 10, (3)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is NZ$431
includes taxes & fees
6 Jan - 7 Jan
Sun Filled Lake House Living
10.0 out of 10, Exceptional, (1)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
8.6 out of 10, Excellent, (4)
"Great Stay at the Olde Tobacco Barn. Was here for a work trip, and the place was perfect for our needs. House is set back really nicely and private. Host was super responsive and easy to deal with. Overall 5/5 stay. Thank you!"
United States
Sgt W.
The price is NZ$844
includes taxes & fees
2 Jan - 3 Jan
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
8.4 out of 10, Very good, (12)
"Great place ! Quiet and safe place! We will be back! "
United States
Aubrey C.
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

Apartment in Plainville

The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (25)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is NZ$789
includes taxes & fees
1 Feb - 2 Feb
The Sun Filled Cozy Creamery
10.0 out of 10, Exceptional, (16)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
United States
Kate B.
Charming apartment 7 minute walk to downtown
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is NZ$628
includes taxes & fees
5 Jan - 6 Jan
Big farmhouse in the foothills of the Berkshires
9.0 out of 10, Wonderful, (2)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
#2 *Beautiful 1 BR Apartment - Central CT*
10.0 out of 10, Exceptional, (23)
"The place was perfect for the two of us. It was close to both our kids homes."
United States
Tomas M.
The price is NZ$420
includes taxes & fees
21 Jan - 22 Jan
River Overlook - Check the view from your deck!
2.0 star property
9.4 out of 10, Exceptional, (3)
"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!! "
United States
Joslynn T.
The price is NZ$1,238
includes taxes & fees
7 Jan - 8 Jan
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
10.0 out of 10, Exceptional, (9)
"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 NZ$1,198
includes taxes & fees
4 Jan - 5 Jan
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
The price is NZ$903
includes taxes & fees
6 Jan - 7 Jan
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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

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 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 NZ$903 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?

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, Burr Pond State Park and Northwestern Connecticut Community College Library 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.