Winchester Holiday Rentals from NZ$487: Search Short-Term Rentals

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Our top choices for Winchester holiday rentals

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

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

winsted

traci

A wooden cabin interior with a bench, a rug, and a hanging plant.

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

Thomas C.

includes taxes & fees

2 Nov - 3 Nov

A two-story house with a front porch, a small balcony, and a white picket fence.

3. Cozy Attic 10 min to Llitchfield

Torrington

Nicole N.

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

4. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

2 Nov - 3 Nov

A wooden wall with a large mirror, a wooden console table, and two wall-mounted lanterns.

5. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Torrington

includes taxes & fees

14 Oct - 15 Oct

A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

6. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

Amanda T.

includes taxes & fees

9 Nov - 10 Nov

7. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

includes taxes & fees

28 Oct - 29 Oct

A balcony with a view of a lake, white railings, and outdoor furniture.

8. River Overlook - What a view from your deck!

Collinsville

Mary S.

includes taxes & fees

14 Oct - 15 Oct

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

9. Sun Filled Lake House Living

Avon

Joseph C.

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

10. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."

Margaret A.

includes taxes & fees

4 Nov - 5 Nov

A square fire pit with flames, surrounded by a grassy field and a green chair.

11. Peaceful Meadow Retreat

Granby

Todd R.

includes taxes & fees

26 Oct - 27 Oct

A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

12. The Historic Hideaway

Avon

Nicole M.

includes taxes & fees

4 Nov - 5 Nov

A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

13. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Cornwall

Candice S.

includes taxes & fees

11 Nov - 12 Nov

A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

14. The Old Avon Village

Avon

Deborah S.

includes taxes & fees

4 Nov - 5 Nov

A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

15. The Sun Filled Cozy Creamery

Plainville

Heather T.

A patio with a table and chairs, a grill, and a view of a lake.

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

Collinsville

Mike

includes taxes & fees

19 Oct - 20 Oct

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

17. Cozy Camper tucked into the woods

Sandisfield

"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...

hannah w.

includes taxes & fees

14 Oct - 15 Oct

A spacious room with a wooden staircase, a dining area with chairs and a table, and a large window with a view of trees.

18. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol

includes taxes & fees

22 Oct - 23 Oct

A deck with a white chair and a table, a sliding glass door, and a potted plant.

19. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol

includes taxes & fees

14 Oct - 15 Oct

A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

20. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

Morris

Joe K.

includes taxes & fees

14 Oct - 15 Oct

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Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

10/10 Excellent

"The front desk staff was so amazing. They helped us from the moment of our arrival. Will definitely stay there again !!!"

The Farmington Inn & Suites

8/10 Good

"The room was nice though a few stains on the bathroom ceiling and the floor creaked a lot when the people above walked around but overall it was very nice. I was looking forward to waffles for breakfast but they were out of batter and I didn’t have a lot of time to wait and find someone to refill it. I enjoyed my stay and would stay again though I thought it was a bit pricey."

Interlaken Inn & Resort

10/10 Excellent

"The Interlaken is a lovely property "between the lakes" in Lakeville. We stayed in the main building, which I recommend (there is also another building on the property with a view of the lake). We had a nice screened-in balcony porch attached to our room which we enjoyed each evening. The lobby is cozy with a fireplace. The staff were friendly and helpful."

Find out more about Winchester

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester. Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester short-term rentals, that won’t be hard to do.

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?

Waterfront House & Guest House Available in Winchester, CT!: This highly rated holiday home rental in Winchester is located on a lake, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals will I find in Winchester?

Expedia has 11 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, The Marina at Highland Lake and Burr Pond 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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Check prices for these dates

Our top choices for Winchester holiday rentals

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

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

3. Cozy Attic 10 min to Llitchfield

4. Art House 3 Beds Close to Warner Theater

5. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

6. Pristine Cozy Walkable Downtown 2BR Getaway

7. Cozy Modern Farmhouse Private Apt - 3 Beds

8. River Overlook - What a view from your deck!

9. Sun Filled Lake House Living

10. Collinsville River Escape / Fall Foliage, Deck & Yard

11. Peaceful Meadow Retreat

12. The Historic Hideaway

13. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

14. The Old Avon Village

15. The Sun Filled Cozy Creamery

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

17. Cozy Camper tucked into the woods

18. Bristol Condo Near ESPN HQ & Lake Compounce!

19. Bristol Condo Near Espn HQ & Lake Compounce!

20. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

Find holiday rentals that suit your style

Top Winchester Hotel Reviews

DoubleTree by Hilton Hotel Bristol, Connecticut

The Farmington Inn & Suites

The Litchfield Inn

Delamar West Hartford

The Abner Hotel

Days Inn by Wyndham Torrington

Sheraton Hartford Hotel at Bradley Airport

Simsbury 1820 House

Interlaken Inn & Resort

Find out more about Winchester

Frequently asked questions

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