Winchester Holiday Rentals

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Holiday Rentals in Winchester

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

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

9.2 out of 10, Wonderful, (37)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass....

9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Spectacular Short Term Vacation Rental in Kent
Exterior

Spectacular Short Term Vacation Rental in Kent

9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Newly renovated cottage on the lake!
Interior

Newly renovated cottage on the lake!

10.0 out of 10, Exceptional, (22)
"We love live live this property. It is perfect for what we need. Our daughter lives just a shirt distance away in Torrington. This is our second time staying in this house. We love it"
Newly renovated cottage on the lake!
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Fridge, microwave, oven, stovetop

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Idillic summer getaway in Litchfield Hills, CT.
Exterior

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.
Serene Acreage - Pond - Hiking Trails Nearby
Terrace/patio

Serene Acreage - Pond - Hiking Trails Nearby

10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is AU$553
includes taxes & fees
20 Dec - 21 Dec
Big farmhouse in the foothills of the Berkshires
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, ping pong, stereo

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.8 out of 10, Exceptional, (19)
"Gorgeous home and property, loved being on the lake with the game room cabana, the outdoor areas are so relaxing, and the home is so tastefully decorated. We enjoyed it so much!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Linny's Updated Lakeview Cottage - Cozy & Modern
Smart TV, DVD player, books, music library

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"The Lakeview Cottage exceeded expectations! My family was visiting from out of state for our daughters’ Cheer Competition and it was the perfect home away from home. Home was clean, Host was very communicative and accommodating, would definitely book again!"
Linny's Updated Lakeview Cottage - Cozy & Modern
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (15)
"This was a great, cozy place for my wife and I to stay in Collinsville. The rooms were tastefully decorated, in great shape, updated, clean, and peppered with cute artwork based on the "when pigs can fly" theme that always brought a smile to my face when I found another one. The queen bed was very comfortable; the kitchen had all of the appliances, dishes, and cookware we needed; the HVAC system was easy to use and kept the rooms at whatever temperature we wanted; and there was a nice deck with...
River Overlook - Check the view from your deck!
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub

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

9.8 out of 10, Exceptional, (25)
"We had a great time staying at Lars place. The hot tub was very relaxing and the location was just what we were looking for to get away for a few days."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (16)
"I had an absolutely wonderful weekend. The home was clean, cozy, and exactly as described in the listing. From the moment I arrived, I felt right at home. Mariana was incredibly responsive and helpful and ensuring I had everything I needed throughout my stay. I will be coming back again."
Cozy & Chic Cabin by the Lake, with access to private Beach!
Perfect Vacation Get Away - Historical New Marlborough
Property grounds

Perfect Vacation Get Away - Historical New Marlborough

9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
Peaceful, Post and Beam Loft, Sleeps 9
1 bedroom, iron/ironing board, WiFi, bed sheets

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
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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Other types of properties in Winchester you may be interested in

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

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

9.2 out of 10, Wonderful, (37)
"We loved the brilliant use of space and all the amenities in this cozy hideaway. My husband, who owns a Professional Organization business, was very pleased and impressed by the clever use of various storage options. The walkways were attractively and effectively lit up for evening strolls and dog walking. All instructions were clearly communicated and our stay was lovely"
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Family House On Highland Lake with Dock
Fridge, microwave, oven, stovetop

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (23)
"Stayed for labor day with family from out of state. Plenty of room for 4 adults and 4 kids, Could have easily fit more. Had a great time on the dock and having fires in the back yard. "
Family House On Highland Lake with Dock
The Farmington Inn & Suites
Staircase

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1065)
"We had a lovely stay. The staff were very kind and attentive to all our needs. The room and accommodations were very nice. "
The price is AU$256
includes taxes & fees
7 Dec - 8 Dec
The Farmington Inn & Suites
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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?

Spectacular Short Term Vacation Rental in Kent: This holiday home rental outside of Winchester is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Expedia has 6 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Highland Lake and Burr Pond State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, Winchester Historical Society 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.