Best Resorts in Winchester

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Jun 27 - Jun 29
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Jul 18 - Jul 20
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Aug 15 - Aug 17

Resorts in Winchester

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Recommended hotels in Winchester

Sheraton Hartford Hotel at Bradley Airport
Executive lounge

Sheraton Hartford Hotel at Bradley Airport

3.5 star property
9.2 out of 10, Wonderful, (1000)
"Great near the airport"
$249 nightly
The price is $286
Jun 25 - Jun 26
Total includes taxes and fees
Sheraton Hartford Hotel at Bradley Airport
Delamar West Hartford
Lunch and dinner served

Delamar West Hartford

4.0 star property
9.8 out of 10, Exceptional, (986)
"Beautiful hotel"
$329 nightly
The price is $376
Jul 1 - Jul 2
Total includes taxes and fees
Delamar West Hartford
Spacious & Private 2BR Near West Hartford Center w Free Parking
Fridge, microwave, oven, stovetop

Spacious & Private 2BR Near West Hartford Center w Free Parking

Spacious & Private 2BR Near West Hartford Center w Free Parking
Premium 3-Story Townhome | Perfect for Large Groups
Fridge, microwave, oven, stovetop

Premium 3-Story Townhome | Perfect for Large Groups

2.0 star property
9.0 out of 10, Wonderful, (4)
"Property as advertised & convenient - nice location. Great communication; appreciate the hospitality! "
$528 nightly
The price is $599
Jun 23 - Jun 24
Total includes taxes and fees
Premium 3-Story Townhome | Perfect for Large Groups
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Interior

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
10.0 out of 10, Exceptional, (2)
"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!! "
$665 nightly
The price is $753
Jun 26 - Jun 27
Total includes taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
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, (5)
"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."
$655 nightly
The price is $742
Jun 26 - Jun 27
Total includes taxes and fees
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford
Extended Stay America Suites Hartford Farmington
Deluxe Studio, Multiple Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets

Extended Stay America Suites Hartford Farmington

2.5 star property
8.0 out of 10, Very Good, (954)
"Friendly staff and clean rooms"
$110 nightly
The price is $127
Jun 29 - Jun 30
Total includes taxes and fees
Extended Stay America Suites Hartford Farmington
Homewood Suites by Hilton Hartford-Farmington
BBQ/picnic area

Homewood Suites by Hilton Hartford-Farmington

3.0 star property
8.4 out of 10, Very Good, (990)
"great location "
$166 nightly
The price is $190
Jul 1 - Jul 2
Total includes taxes and fees
Homewood Suites by Hilton Hartford-Farmington
Hampton Inn & Suites Hartford/Farmington
Exterior

Hampton Inn & Suites Hartford/Farmington

2.5 star property
8.8 out of 10, Excellent, (1000)
"Staff was very friendly and prompt, whole facility was clean and nice, breakfast was delicious and the grounds were gorgeous. Will definitely stay there when traveling to that area again!"
$149 nightly
The price is $172
Jul 2 - Jul 3
Total includes taxes and fees
Hampton Inn & Suites Hartford/Farmington
Fairfield Inn & Suites by Marriott Plainville
Lobby

Fairfield Inn & Suites by Marriott Plainville

2.5 star property
8.6 out of 10, Excellent, (838)
"Very clean , comfortable beds and friendly staff "
$105 nightly
The price is $121
Jul 3 - Jul 4
Total includes taxes and fees
Fairfield Inn & Suites by Marriott Plainville
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
Property grounds

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

$434 nightly
The price is $493
Jun 20 - Jun 21
Total includes taxes and fees
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do
The Farmington Inn & Suites
Interior

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1001)
"We have stayed at the Farmington Inn many times and it has consistently been a positive experience! The rooms are comfortable and clean while the staff is friendly and accommodating. It is by far our favorite place to stay when visiting Farmington. "
$148 nightly
The price is $171
Jun 23 - Jun 24
Total includes taxes and fees
The Farmington Inn & Suites
Avon Old Farms Hotel
Interior

Avon Old Farms Hotel

3.5 star property
8.4 out of 10, Very Good, (1001)
"Good place to stay"
$188 nightly
The price is $216
Jun 29 - Jun 30
Total includes taxes and fees
Avon Old Farms Hotel
Simsbury 1820 House
Front of property

Simsbury 1820 House

4.0 star property
9.2 out of 10, Wonderful, (967)
"Great place to stay! "
$204 nightly
The price is $235
Jun 29 - Jun 30
Total includes taxes and fees
Simsbury 1820 House
Simsbury Inn
Exterior

Simsbury Inn

3.5 star property
9.2 out of 10, Wonderful, (255)
"Front desk personnel excellent!"
$248 nightly
The price is $285
Jun 29 - Jun 30
Total includes taxes and fees
Simsbury Inn
#2 *Beautiful 1 BR Apartment - Central CT*
Fridge, microwave, oven, stovetop

#2 *Beautiful 1 BR Apartment - Central CT*

8.0 out of 10, Very Good, (1)
"Check in was easy. Communication with host was swift. Great Bed. Pretty basic amenities. Would definitely rent from them again. "
$143 nightly
The price is $154
Jun 22 - Jun 23
Total includes taxes and fees
#2 *Beautiful 1 BR Apartment - Central CT*
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
Fridge, microwave, oven, stovetop

#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!

8.8 out of 10, Excellent, (6)
"We were in Connecticut for our nephew's wedding and the house was an excellent alternative to getting hotel rooms. Roomy and comfortable, it made for a great stay and allowed for fun mealtime conversations and visits from local family members."
$223 nightly
The price is $243
Jun 22 - Jun 23
Total includes taxes and fees
#3 FRESHLY REDONE & NEWLY FURNISHED! A MUST SEE!
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Fridge, microwave, oven, stovetop

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

10.0 out of 10, Exceptional, (2)
"This property suited our families needs perfectly. It was very clean and as advertised. Host was very quick and responsive to questions. Highly recommend!!!"
$615 nightly
The price is $667
Jun 22 - Jun 23
Total includes taxes and fees
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10
Historic Hideaway
Private kitchen

Historic Hideaway

2.0 star property
$335 nightly
The price is $380
Jul 10 - Jul 11
Total includes taxes and fees
Historic Hideaway
Old Avon Village
Private kitchen

Old Avon Village

2.0 star property
6.0 out of 10, (4)
"We had a nice stay while visiting our son at AOF. There were a couple of small issues which the owner remedied IMMEDIATELY. Things happen in life which are unforeseen, we appreciated the owner jumping on the issues quickly."
$302 nightly
The price is $342
Jun 22 - Jun 23
Total includes taxes and fees
Old Avon 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.
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Frequently asked questions

What is Winchester like for a resort vacation?
Longing for a relaxing escape? Indulge in all the comforts of a resort, where you can find everything you want for your trip from convenient dining options to activities and shopping. Browse the resorts in the area and discover the right one for you, whether you envision yourself sipping drinks by a sprawling pool or checking out the on-site boutiques.
What's a top resort for my stay in Winchester?
Our top-rated resort near Winchester: Lakeview Cottage with Dock, Kayaks - 17 mi (27.3 km) from Winchester.
What can I do in Winchester?
Discover the shopping possibilities at Ledgebrook Plaza, or bring the kids to KidsPlay Museum for some family fun. Additional attractions in the area include Highland Lake and Burr Pond State Park.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What's the best way to get to and around Winchester?
Fly into Bradley Intl. Airport (BDL), which is located 21.9 mi (35.2 km) away from the heart of the city. Otherwise, look for flights into Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.