Watertown Vacations from $570

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Your Watertown Vacation

Lock in a Watertown vacation package and get set to experience the best of this city. Consider staying in the neighborhood of Washington, which is great for nature, history and views. Every good trip to Watertown should include a bit of sightseeing. What to do first? Black Rock State Park and Flanders Nature Center are main attractions. Stop dreaming and start doing. Check out the wide range of options on Expedia today and put your Watertown vacation plans into action!

The Latest Watertown 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 $712, price is now $570 per person
$570
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.6/10 Excellent! (1,105 reviews)
Comfortable hotel, right in the heart of New Haven. Easy access to city and University. Rooms were clean and comfortable. I would stay there again.

Reviewed on Nov 1, 2026

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
Price was $758, price is now $626 per person
$626
per person
Jan 24 - Jan 31
found 7 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
7.4/10 Good! (1,004 reviews)
Staff were fantastic and friendly, shower was awesome and mini k cup coffee maker was addictive.

Reviewed on Nov 1, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $721, price is now $601 per person
$601
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $939, price is now $786 per person
$786
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was $777, price is now $672 per person
$672
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (2 reviews)

Don't see what you're looking for?
See all available trips from Pretty Prairie to Watertown
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Stay near popular Watertown attractions

Lake Winnemaug

Commune with nature and explore the great outdoors at Lake Winnemaug during your travels in Watertown. While you're in the area, wander around the parks.
See properties

Watertown Hotel Deals

Cozy cottage with AC and lake access in charming Connecticut suburb.

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown CT
9.6/10 Exceptional! (19 reviews)
"Very nice place great host nice clean place very well located definitely served the purpose for my visit will stay again"

Reviewed on Oct 16, 2026

Get rates
Cozy cottage with AC and lake access in charming Connecticut suburb.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$109 nightly
The price is $125 total per night from Dec 2 to Dec 3
$125 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (1,466 reviews)
"All ok. No complaints ."

Reviewed on Nov 1, 2026

Holiday Inn Express Southington by IHG
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $149 total per night from Nov 4 to Nov 5
$149 total
Nov 4 - Nov 5
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"This is a very tired looking and feeling hotel. The hallway carpets are worn and dingy. The lobby smells very strongly of vanilla, as if they are trying to cover up some other odor. The elevator interior is banged up. The rooms look drab, and the doors don't seal well, so hallway noise comes right ..."

Reviewed on Nov 1, 2026

Heritage Hotel, Golf & Conference Center
See all 859 properties in Watertown
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 Watertown Vacation Packages

Watertown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
3,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Woodbury Ski Area, Pilgrim Mall Shopping Center and Glebe House Museum and The Gertrude Jekyll Garden

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Frequently asked questions

How much does a Watertown vacation package cost?
You can pick up a vacation package to this destination from $570 on Expedia. But how much your vacation to Watertown costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Watertown?
If you're hoping to score a cheap Watertown vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Watertown?
With a well-organized travel plan, you can easily visit the top Watertown sights in a few days. But if you'd like to discover hidden gems or go on day trips, think about booking your Watertown vacation for longer.
How to find the best Watertown package deals?
Use Expedia's filter tool to find some fabulous Watertown package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Watertown package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Watertown vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can personalize your Watertown getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Watertown?
If you've got your Watertown vacation dates confirmed, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Watertown vacation packages?
If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Watertown trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.