Winchester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 7 - Dec 8
Tomorrow
Dec 8 - Dec 9
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Vacation Rentals in Winchester

Fridge, microwave, oven, stovetop
Family House On Highland Lake with Dock

Family House On Highland Lake with Dock

Winsted
10.0 out of 10, Exceptional, (28)
"Great house for access to Highland lake. Stayed w/ another family and layout was good for multiple people. Owner very responsive. Would stay again. "
United States
TJ M.
Family House On Highland Lake with Dock
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Northwest Harwinton
8.8 out of 10, Excellent, (28)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth
9.8 out of 10, Exceptional, (40)
"Our stay was so peaceful and relaxing. The property was beautiful and exactly as described in the listing. We loved having a fire outside, sitting in the screened-in porch. Will absolutely be coming back!"
United States
Jean R.
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Cornwall
9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Outdoor dining
The Goshen Glass Chalet

The Goshen Glass Chalet

Goshen
9.6 out of 10, Exceptional, (42)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet
Interior
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 ￥44,766
￥106,856 total
includes taxes & fees
Dec 11 - Dec 12
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Exterior
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
9.8 out of 10, Exceptional, (94)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Exterior
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage
Fridge, microwave, oven, stovetop
Linny’s Lake Retreat, Family-Friendly & Dock Access

Linny’s Lake Retreat, Family-Friendly & Dock Access

West Suffield
9.8 out of 10, Exceptional, (27)
"Very peaceful in a beautiful setting and the house with the updates is well decorated and furnished. Beds were comfortable. Beach chairs provided as well. Very well accommodated. We enjoyed our stay!"
United States
kristen u.
Linny’s Lake Retreat, Family-Friendly & Dock Access
Exterior
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Watertown
9.6 out of 10, Exceptional, (16)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Fridge, microwave, oven, stovetop
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)
"A very nice period home in a beautiful setting. The home is immaculate with all of the necessary essentials for an extended stay. The host is very responsive and keeps in touch to ensure that your stay is as enjoyable and comfortable as possible. "
United States
Virginia M.
The price is ￥40,401
￥70,577 total
includes taxes & fees
Dec 9 - Dec 10
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Property grounds
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 ￥24,697
￥71,273 total
includes taxes & fees
Dec 9 - Dec 10
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥31,066
￥56,972 total
includes taxes & fees
Dec 9 - Dec 10
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT

Bloomfield
The price is ￥51,771
￥162,055 total
includes taxes & fees
Dec 14 - Dec 15
Family-Friendly Retreat - Sleeps 20 in Bloomfield, CT
Exterior
Cozy & Serene Cabin with Fireplace, Ski Nearby!

Cozy & Serene Cabin with Fireplace, Ski Nearby!

Bethlehem
10.0 out of 10, Exceptional, (35)
"Awesome location and cottage. So peaceful and easy. Would 100% book again "
United States
Leah G.
Cozy & Serene Cabin with Fireplace, Ski Nearby!
Property grounds
Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events

2.0 star property
Bloomfield
10.0 out of 10, Exceptional, (4)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
The price is ￥44,766
￥106,856 total
includes taxes & fees
Dec 9 - Dec 10
Stylish Townhome | Perfect for Family Gatherings & Events
Terrace/patio
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Barkhamsted
10.0 out of 10, Exceptional, (3)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Spain
Heather A.
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Interior
Group-Friendly Townhouse Stay – Sleeps up to 20

Group-Friendly Townhouse Stay – Sleeps up to 20

Bloomfield
The price is ￥51,259
￥164,728 total
includes taxes & fees
Dec 11 - Dec 12
Group-Friendly Townhouse Stay – Sleeps up to 20
Interior
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Great Barrington
9.8 out of 10, Exceptional, (14)
"Very enjoyable stay, highly recommended."
United States
Niall M.
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

10/10 Excellent
"Clean room and great staff"
Beth 3-night trip
Posted 3 days ago
Hampton Inn & Suites Hartford/Farmington

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Are there vacation rentals in Winchester?

Yes, there are vacation rentals in Winchester close to Laurel Lanes, or you can choose a more remote option if you're looking for extra privacy while you relax.

What are some of the best vacation rentals that Winchester has to offer?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This vacation home rental near Winchester is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Winchester?

Expedia has 7 vacation 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 Winchester Historical Society are other places worth a visit.

What’s a vacation rental in Winchester like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.