Watertown Vacations from $299

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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.
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 $366, price is now $299 per person
$299
per person
Mar 13 - Mar 16
found 3 hours ago
Roundtrip flight included
Raleigh (RDU) 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
Price was $2,268, price is now $1,193 per person
$1,193
per person
Mar 19 - Mar 23
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
No reviews

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Save 100% on your flight
Price was $652, price is now $470 per person
$470
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 $487, price is now $359 per person
$359
per person
Mar 13 - Mar 16
found 3 hours ago
Roundtrip flight included
Raleigh (RDU) 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

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $778, price is now $597 per person
$597
per person
Mar 13 - Mar 16
found 3 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
Very quiet, clean and peaceful accommodation. Enjoyed our stay here. Very spacious apartment with everything you need for a comfortable stay. Felt right at home - away from home. Highly recommend.

Reviewed on Jan 7, 2026

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Watertown Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$87 nightly
The price is $100 total per night from Feb 1 to Feb 2
$100 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (1,195 reviews)
Clean comfortable room, friendly staff, great breakfast

Reviewed on Jan 2, 2026

Holiday Inn Express Southington by IHG
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Jan 25 to Jan 26
$102 total
Jan 25 - Jan 26
Total with taxes and fees
8.2/10 Very Good! (1,099 reviews)
A wonderful staff and clean rooms

Reviewed on Jan 5, 2026

Courtyard by Marriott Waterbury Downtown
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
See all 816 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 $299 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.