Winchester Vacation Rentals

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Winchester vacation rentals

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)
"Great little place, beutiful view to enjoy your coffee."
United States
Shaun H.
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
Exterior
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont
9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
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.
$607 nightly
The price is $688
Dec 11 - Dec 12
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
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
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
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 House with dock

Linny’s Lake House with dock

West Suffield
9.8 out of 10, Exceptional, (27)
"We had an amazing time really nice neighborhood. We'll definitely be back next year."
United States
Aimee W.
Linny’s Lake House with dock
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)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
United States
Jeanmarie G.
$401 nightly
The price is $454
Dec 10 - Dec 11
Total with taxes and fees
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.
$394 nightly
The price is $446
Dec 10 - Dec 11
Total with taxes and fees
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.
$344 nightly
The price is $364
Dec 10 - Dec 11
Total with taxes and fees
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
$915 nightly
The price is $1,040
Dec 11 - Dec 12
Total with taxes and fees
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!
Interior
Group-Friendly Townhouse Stay – Sleeps up to 20

Group-Friendly Townhouse Stay – Sleeps up to 20

Bloomfield
$936 nightly
The price is $1,061
Dec 11 - Dec 12
Total with taxes and fees
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
Exterior
Summer Lake Cottage, private beach, Berkshire Hills, small village

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville
9.4 out of 10, Exceptional, (84)
"The location was perfect for racing at Lime Rock Park."
United States
Jane D.
Summer Lake Cottage, private beach, Berkshire Hills, small village
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

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

10/10 Excellent
"Clean room, staff were friendly, helpful and kind. Quiet even with planes landing right next door. Can't compliment this place enough."
Christine 1-night trip
Posted 22 hours ago
Sheraton Hartford Hotel at Bradley Airport

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $364 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.