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Wooster Square Vacation Packages

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Wooster Square Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Crystal Bees and Hawks Landing Country Club are located nearby.
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Vintage Radio and Communications Museum of Connecticut and Oliver Ellsworth Homestead are located nearby.
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Crystal Bees and Barnes Museum are located nearby.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions XL Center and Vintage Radio and Communications Museum of Connecticut are located nearby.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Barnes Museum and Southington Public Library are located nearby.
Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in South Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Promenade Shops at Evergreen Walk and Shoppes at Buckland Hills are located nearby.
Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Vintage Radio and Communications Museum of Connecticut and Oliver Ellsworth Homestead are located nearby.
Simsbury Inn

Simsbury Inn

3.5 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Stay at this 3.5-star business-friendly hotel in Weatogue. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosedale Farms & Vineyards and Stratton Brook State Park are located nearby.
Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Stay at this 3.5-star business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Vintage Radio and Communications Museum of Connecticut and Windsor Historical Society are located nearby.

3-4 Night Vacations in Wooster Square

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
The Captain Stannard B&B Country Inn

The Captain Stannard B&B Country Inn

3 out of 5
Westbrook Center
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
Dec 26 - Dec 29
found 2 days ago
Roundtrip flight included
West Palm Beach (PBI) to New Haven (HVN)

5-7 Night Vacations in Wooster Square

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to New Haven (HVN)

Wooster Square Last Minute Hotel Deals

New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
New Haven Hotel
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
Book a stay at this business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Omni New Haven Hotel at Yale
Hotel Marcel New Haven, Tapestry Collection By Hilton
Hotel Marcel New Haven, Tapestry Collection By Hilton
4 out of 5
500 Sargent Drive, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hotel Marcel New Haven, Tapestry Collection By Hilton
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
2.5 out of 5
400 Sargent Dr, New Haven, CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
La Quinta Inn & Suites by Wyndham New Haven
The Blake Hotel
The Blake Hotel
4 out of 5
9 High Street, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
The Blake Hotel
Cambria Hotel New Haven University Area
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Cambria Hotel New Haven University Area
New Haven Village Suites
New Haven Village Suites
3 out of 5
3 Long Wharf Dr, New Haven, CT
Book a stay at this business-friendly aparthotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
New Haven Village Suites
Graduate by Hilton New Haven
Graduate by Hilton New Haven
4 out of 5
1151 Chapel Street, New Haven, CT
Stay at this 4-star hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and free bicycles on site. Our guests praise the helpful staff and the comfy ...
Graduate by Hilton New Haven
See all 578 properties in Wooster Square
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.

Book the perfect getaway to Wooster Square

With Hotwire, booking your next trip to Mill River is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Wooster Square while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Wooster Square flight and hotel package for as low as $436.

Living it up in Mill River means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Wooster Square, Mill River vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Wooster Square for some of the best accommodations and flight deals.

FAQs about cheap Wooster Square packages:

How to get cheap vacation deals to Wooster Square?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $113.

How much are Wooster Square packages?

Vacation packages to Wooster Square vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $436.

How to find cheap car rentals near Wooster Square?

Hotwire partners with some of the most reliable car rental companies in Mill River to bring you the best car rental deals in Wooster Square for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Wooster Square now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Wooster Square right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.