Winchester Vacation Rentals

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Oct 17 - Oct 19
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Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Winchester

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

Family House On Highland Lake with Dock

10.0 out of 10, Exceptional, (28)
"Awesome location, plenty of space in the house, clean, and the host was very responsive. Will definitely stay here again when in Connecticut. "
Family House On Highland Lake with Dock
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

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

8.8 out of 10, Excellent, (24)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (82)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

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

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
$362 nightly
The price is $404
Oct 5 - Oct 6
Total with taxes and fees
The Blue Elm - A Historic Berkshire Cottage
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
$994 nightly
The price is $1,125
Oct 25 - Oct 26
Total with taxes and fees
Whispering Estate Guest House - A Romantic Countryside Getaway
Guesthouse Cabin vacation rentals in Berkshire County
Dining

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
$622 nightly
The price is $695
Oct 2 - Oct 3
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

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

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (21)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
The Goshen Glass Chalet
Outdoor dining

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (61)
"There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. "
$433 nightly
The price is $491
Oct 13 - Oct 14
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
The Sun Filled Cozy Creamery
TV

The Sun Filled Cozy Creamery

8.8 out of 10, Excellent, (21)
"Nice,cozy and a reasonable rate."
$261 nightly
The price is $279
Oct 4 - Oct 5
Total with taxes and fees
The Sun Filled Cozy Creamery
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Fridge, microwave, oven, stovetop

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.2 out of 10, Wonderful, (7)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
$479 nightly
The price is $544
Oct 5 - Oct 6
Total with taxes and fees
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Terrace/patio

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

10.0 out of 10, Exceptional, (2)
"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."
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Fridge, microwave, oven, stovetop

Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi

10.0 out of 10, Exceptional, (1)
"Clean and quiet location, great place for a relaxing stay."
Spacious 4-bedroom Modern Architecture Cozy Getaway with Fitness Room, WiFi
Private Island - Largest Fresh Water Reservoir in Mass
Interior

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Westfield Vacation Rental w/ Porch, Pets Welcome!
House (3 Bedrooms) | Interior

Westfield Vacation Rental w/ Porch, Pets Welcome!

3.0 star property
Westfield Vacation Rental w/ Porch, Pets Welcome!
Bluebird Valley Farmhouse
Property grounds

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (69)
"We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!"
Bluebird Valley Farmhouse
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Exterior

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

9.6 out of 10, Exceptional, (14)
"The house is huge with plenty of room and tons of features! Pool and hot tubs were lots of fun and the game room is full of games and tables to keep the kids happy.The location is very secluded and private, with easy access to stores and restaurants right down the street if needed.Brian was very responsive and easy to work with before and during our stay."
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
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

Simsbury Inn

Simsbury Inn

10/10 Excellent
"I loved my stay there. Beautiful rooms, the hot tub was great! Breakfast was decent but there are plenty of food options around town if you want something better!"
Caitlin 3-night trip
Posted 1 day ago
Simsbury Inn

Find out more about Winchester

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 $404 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

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?

Whispering Estate Guest House - A Romantic Countryside Getaway: This vacation home near Winchester offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

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, Burr Pond State Park and Platt Hill State Park 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.