Harwinton Vacations from $396

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Your Harwinton Vacation

When a city break is calling, answer it with a vacation package to Harwinton. The neighborhood of Litchfield Historic District, which is good for shopping, dining and history, makes a wonderful base for your adventures. A trip to Harwinton wouldn't be complete without swinging by a few well-known attractions, such as Connecticut Valley Winery. Whoever you're traveling with and whatever your bank balance, your dream Harwinton vacation is just clicks away with Expedia.

The Latest Harwinton vacation packages

Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $489, price is now $396 per person
$396
per person
Apr 24 - Apr 26
found 7 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
8.6/10 Excellent! (1,004 reviews)
Will always book here it was beautiful and staff was great love it 10/10

Reviewed on Mar 7, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,326, price is now $1,029 per person
$1,029
per person
May 28 - May 31
found 8 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (958 reviews)
Groovy, fun, comfortable hotel in a great location.

Reviewed on Mar 3, 2026

52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay

52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay

3 out of 5
Save 100% on your flight
Price was $2,212, price is now $1,735 per person
$1,735
per person
May 24 - May 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Westfield (BAF)
No reviews
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,832, price is now $1,446 per person
$1,446
per person
May 17 - May 19
found 3 hours ago
Roundtrip flight included
Orlando (ORL) to New Haven (HVN)
9.2/10 Wonderful! (29 reviews)
Communication and ease

Reviewed on Mar 8, 2026

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Price was $1,006, price is now $818 per person
$818
per person
May 17 - May 19
found 3 hours ago
Roundtrip flight included
Orlando (ORL) to New Haven (HVN)
9.4/10 Exceptional! (347 reviews)
beautiful room and views

Reviewed on Dec 13, 2025

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Discover the most popular places to visit in Harwinton

Harwinton Conservation and Recreation Area

Explore the great outdoors at Harwinton Conservation and Recreation Area, a lovely green space in Harwinton. Discover the bars and live music in this relaxing area.

Harwinton Conservation and Recreation Area

Harwinton Hotel Deals

Argyll House by Boutique

Argyll House by Boutique

2 out of 5
Harwinton CT
Get rates
Argyll House by Boutique
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Mar 29 to Mar 30
$108 total
Mar 29 - Mar 30
Total with taxes and fees
7.6/10 Good! (1,195 reviews)
A solid OK hotel. It's very evident there is no brand standard. The room is dated and in need of repairs. I recommend having a white noise machine because this is next to a train station and they can keep you up all night. The continental breakfast was comical. They serve cut up hot dogs as your ...

Reviewed on Mar 12, 2026

The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $101 total per night from Mar 21 to Mar 22
$101 total
Mar 21 - Mar 22
Total with taxes and fees
8.6/10 Excellent! (1,233 reviews)
Breakfast was not the best but good.

Reviewed on Mar 11, 2026

Holiday Inn Express Southington by IHG
See all 796 properties in Harwinton
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 Harwinton Vacation Packages

Harwinton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Connecticut Valley Winery, Winchester Historical Society and Jerram Winery

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Frequently asked questions

How much does a Harwinton vacation package cost?
Offering excellent value package deals from $396 on Expedia, you'll be pleasantly surprised at how much a vacation to Harwinton costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Harwinton?
November, December and January are the best times to search for cheap Harwinton vacation packages. Traveling in quieter periods means you can typically find better prices on hotels and flights.
How many days is enough for Harwinton?
Typically, a handful of days is enough to visit the top attractions during your Harwinton vacation. However, if you'd like to have some time to kick back or go on day tours, think about extending your trip.
How to find the best Harwinton package deals?
Use Expedia's handy filters to help you find some great Harwinton package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Harwinton package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Harwinton vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can tailor your Harwinton escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Harwinton?
If you're planning a spontaneous Harwinton adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Harwinton vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Harwinton vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.