Deals on vacations and trips to Winsted
Save when you book Winsted package deals
Winsted flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Milford - New Haven
Price was $555, price is now $492 per person
$492
per person
Jun 13 - Jun 16
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.
Beechmont - Perfect for Family Retreat!
North End
Save 100% on your flight
Price was $2,039, price is now $1,302 per person
$1,302
per person
Jun 25 - Jun 28
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Cambria Hotel New Haven University Area
West River
Price was $924, price is now $804 per person
$804
per person
Jun 19 - Jun 22
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.
Springhill Suites Milford
Price was $774, price is now $701 per person
$701
per person
Jun 13 - Jun 16
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Trumbull Marriott Shelton
Price was $676, price is now $626 per person
$626
per person
Jun 13 - Jun 16
found 14 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
Top Winsted hotels deals
The Farmington Inn & Suites
827 Farmington Ave Farmington CT
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $166 total per night
$166 total
Apr 27 - Apr 28
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the free continental breakfast each morning.
Breakfast included
Pet friendly
Holiday Inn Express & Suites Bradley Airport by IHG
600 Spring St Windsor Locks CT
Free Cancellation
$130 nightly
The price is $150 total per night
$150 total
May 4 - May 5
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the free continental breakfast each morning.
Pool
Breakfast included
Sheraton Hartford Hotel at Bradley Airport
1 Bradley International Airport Windsor Locks CT
Free Cancellation
Reserve now, pay when you stay
$246 nightly
The price is $283 total per night
$283 total
Apr 18 - Apr 19
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a computer station are also offered.
Pet friendly
Free WiFi
DoubleTree by Hilton Hartford - Bradley Airport
16 Ella T. Grasso Turnpike Windsor Locks CT
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $150 total per night
$150 total
Apr 19 - Apr 20
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Pool
Free airport shuttle
Delamar West Hartford
1 Memorial Road West Hartford CT
Free Cancellation
Reserve now, pay when you stay
$392 nightly
The price is $448 total per night
$448 total
May 7 - May 8
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free valet parking and free WiFi. Free self parking, a 24-hour business center, and a terrace are also offered.
Spa
Pet friendly
Avon Old Farms Hotel
279 Avon Mountain Rd Avon CT
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $171 total per night
$171 total
Apr 18 - Apr 19
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and WiFi in public areas. You'll appreciate the sauna, bar/lounge, and wedding services.
Pool
Breakfast included
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.
Popular places to visit
Highland Lake
Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
Northwestern Connecticut Community College
Walk around the campus at Northwestern Connecticut Community College as part of your travels around Winchester.
American Mural Project
You can spend time studying the exhibits at American Mural Project in Winchester.
Frequently asked questions
Photos of local treasures
Browse Winsted vacation photos for more inspiration
