Winchester Vacations from $457

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Your Winchester Vacation

The best way to experience this unique city is with a tailor-made Winchester vacation package. Base yourself in the neighborhood of New Hartford, which is good for nature, history and skiing or choose someplace else — our package deals are all about you. Make your trip to Winchester even more enjoyable by going sightseeing. Highland Lake, Laurel Lanes and Winchester Historical Society are some of the leading attractions you'll want to explore. Whatever your travel plans or budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
Price was $549, price is now $457 per person
$457
per person
Mar 16 - Mar 23
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
7/10 Good! (1,001 reviews)
The man the helped check me in was super nice. I picked this place because i had an 8am flight & it was very close to the airport. Also the rate was reasonable. The room next door had loud music playing, so i called the front desk. Within 10 - 15 min they turned it down.

Reviewed on Dec 2, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,774, price is now $986 per person
$986
per person
Mar 6 - Mar 9
found 17 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
No reviews

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Price was $1,197, price is now $821 per person
$821
per person
Mar 16 - Mar 23
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
No reviews
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $705, price is now $550 per person
$550
per person
Mar 16 - Mar 23
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
The room was nice and the staff seemed friendly.

Reviewed on Jan 8, 2026

Clarion Inn

Clarion Inn

3 out of 5
Price was $647, price is now $540 per person
$540
per person
Mar 16 - Mar 23
found 24 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
7.6/10 Good! (1,002 reviews)
Excellent room and front desk lady was very polite

Reviewed on Dec 26, 2025

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Discover the most popular places to visit in Winchester

Winchester Historical Society

You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.

Winchester Historical Society

Winchester Hotel Deals

Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $263 total per night from Jan 30 to Jan 31
$263 total
Jan 30 - Jan 31
Total with taxes and fees
9/10 Wonderful! (1,013 reviews)
I arrived at 2 am and front desk was able to get me into a room at a great rate so I could get a few hours of sleep. Thank you!

Reviewed on Jan 4, 2026

Sheraton Hartford Hotel at Bradley Airport
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $92 total per night from Feb 2 to Feb 3
$92 total
Feb 2 - Feb 3
Total with taxes and fees
7.8/10 Good! (999 reviews)
Great place.

Reviewed on Jan 2, 2026

Extended Stay America Suites Hartford Farmington
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $121 total per night from Jan 11 to Jan 12
$121 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Always cozy with lovely staff. The pet-friendly rooms are great. Love the breakfast and the afternoon cookies/tea!

Reviewed on Jan 2, 2026

The Farmington Inn & Suites
See all 681 properties in Winchester
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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Top Sights
Winchester Historical Society, Laurel Lanes and Platt Hill State Park

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $457 on Expedia for your Winchester escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
November, December and January are the best times to search for cheap Winchester vacation packages. Traveling in less busy months means you can typically find lower prices on accommodations and flights.
How many days is enough for Winchester?
The ideal duration for your Winchester vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the main attractions and explore some hidden gems along the way.
How to find the best Winchester package deals?
Use Expedia's filters to help you find some great Winchester package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Winchester package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a customized Winchester vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winchester?
If you've got your Winchester travel dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester getaway should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.