Winchester Vacations from $340

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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.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $400, price is now $340 per person
$340
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
8/10 Very Good! (1,457 reviews)
Good spot can’t complain about it

Reviewed on Jan 10, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,878, price is now $1,089 per person
$1,089
per person
Feb 13 - Feb 16
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
No reviews
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $547, price is now $424 per person
$424
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Great staff, convenient central location, and tasteful retro-collegiate decor in a renovated historic building.

Reviewed on Jan 1, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $461, price is now $383 per person
$383
per person
Apr 1 - Apr 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
8.6/10 Excellent! (1,184 reviews)
The room was clean and cared for all weekend. The staff was pleasant. The only negative was the amount of light that floods in from the street all night long. The hotel needs curtains or some sort of valance to block out the light that comes in along the top of the window shades. Hard to sleep being beamed in the eyes with so much light.

Reviewed on Jan 12, 2026

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $685, price is now $575 per person
$575
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
Clean and nice! Really appreciated the bath robes.

Reviewed on Jan 2, 2026

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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! (1,000 reviews)
Perfect stay before a long flight.

Reviewed on Jan 7, 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
$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
$126 nightly
The price is $145 total per night from Feb 1 to Feb 2
$145 total
Feb 1 - Feb 2
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 675 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 $340 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.