Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (46)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AU$254
includes taxes & fees
28 Dec - 29 Dec
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

The Historic Hideaway

The Historic Hideaway
2.0 star property
Avon
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 AU$389
includes taxes & fees
12 Jan - 13 Jan 2026
The Historic Hideaway

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
Goshen
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 AU$936
includes taxes & fees
4 Jan - 5 Jan 2026
CT Gate House Goshen CT, Gate House Goshen CT

Peaceful Meadow Retreat

Peaceful Meadow Retreat
2.0 star property
Granby
10.0 out of 10, Exceptional, (16)
"Beautiful property comfy, cozy and clean little cottage."
United States
Denise T.
The price is AU$279
includes taxes & fees
6 Jan - 7 Jan 2026
Peaceful Meadow Retreat

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Torrington
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 AU$515
includes taxes & fees
30 Dec - 31 Dec
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
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

Sun Filled Lake House Living

Sun Filled Lake House Living
2.0 star property
Avon
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 AU$380
includes taxes & fees
7 Jan - 8 Jan 2026
Sun Filled Lake House Living

Charming 1-bedroom in welcoming West Hartford with WiFi, AC

Charming 1-bedroom in welcoming West Hartford with WiFi, AC
West Hartford
The price is AU$191
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 1-bedroom in welcoming West Hartford with WiFi, AC

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
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 AU$658
includes taxes & fees
3 Jan - 4 Jan 2026
The Sun Filled Cozy Creamery

Charming apartment 7 minute walk to downtown

Charming apartment 7 minute walk to downtown
Torrington
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.
The price is AU$391
includes taxes & fees
1 Jan - 2 Jan 2026
Charming apartment 7 minute walk to downtown

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
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 AU$574
includes taxes & fees
30 Dec - 31 Dec
Cozy Modern Farmhouse Private Apt - 3 Beds

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)
"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 AU$770
includes taxes & fees
2 Jan - 3 Jan 2026
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10
2.0 star property
Bloomfield
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 AU$1,074
includes taxes & fees
13 Jan - 14 Jan 2026
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Private Modern 3 Bed Apt Close to Downtown- 1st Flr

Private Modern 3 Bed Apt Close to Downtown- 1st Flr
Torrington
9.0 out of 10, Wonderful, (2)
"Host was very communicative.Perfect location for our needs"
United States
Beth M.
Private Modern 3 Bed Apt Close to Downtown- 1st Flr

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, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
The price is AU$772
includes taxes & fees
29 Dec - 30 Dec
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

#31 - Downtown Terryville- 1 Br

#31 - Downtown Terryville- 1 Br
Plymouth
10.0 out of 10, Exceptional, (1)
"In convenient safe area. Os is easy to contact"
United States
Gina P.
The price is AU$560
includes taxes & fees
31 Dec - 1 Jan 2026
#31 - Downtown Terryville- 1 Br

The Old Avon Village

The Old Avon Village
2.0 star property
Avon
6.2 out of 10, (10)
"My unit was exactly as described. I thoroughly enjoyed my stay and will definitely return again. "
United States
Carol S.
The price is AU$574
includes taxes & fees
7 Jan - 8 Jan 2026
The Old Avon Village

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Plainville
10.0 out of 10, Exceptional, (3)
"Great weekend with friends!"
United States
Neil R.
The price is AU$1,166
includes taxes & fees
31 Dec - 1 Jan 2026
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
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.
The price is AU$473
includes taxes & fees
31 Dec - 1 Jan 2026
#2 *Beautiful 1 BR Apartment - Central CT*

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is AU$1,828
includes taxes & fees
26 Dec - 27 Dec
Whispering Estate Guest House - A Romantic Countryside Getaway
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 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?

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 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 The Marina at Highland Lake 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.