Deals on vacations and trips to Winsted

Save when you book Winsted package deals

Choose two or more items and save on your trip:

Winsted flight + hotel vacation packages

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
Price was $711, price is now $522 per person
$522
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,206, price is now $942 per person
$942
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $836, price is now $618 per person
$618
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $855, price is now $635 per person
$635
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $8,810, price is now $6,558 per person
$6,558
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. Enjoy the sauna and perks like free self parking.

Top Winsted hotels deals

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT
Get rates
A gym is featured at this vacation home, along with a garden and laundry facilities.
Kitchen
Washer
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
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
Aug 18 - Aug 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
Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

2.5 out of 5
600 Spring St Windsor Locks CT
Free Cancellation
$118 nightly
The price is $136 total per night
$136 total
Aug 23 - Aug 24
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
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
2 Farm Glen Blvd Farmington CT
$141 nightly
The price is $162 total per night
$162 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.
Pool
Breakfast included
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $161 total per night
$161 total
Aug 25 - Aug 26
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
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd Avon CT
Free Cancellation
Reserve now, pay when you stay
$172 nightly
The price is $197 total per night
$197 total
Aug 23 - Aug 24
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
Don't see what you're looking for?
See all available properties in Winsted
View all properties
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.

Stay near popular Winsted attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

Frequently asked questions

How much are vacation packages to Winsted?
Travelocity offers great package deals to Winsted, including flights and hotels, starting from as low as $522. With all the extra money, you could include some awesome tours or perhaps even add a few extra nights to your adventure.
Where can I get the best vacation package deals for Winsted?
Whatever your travel style, Travelocity can help you lock in a great Winsted package deal. All you have to do is mix and match from our 400 airlines and 1,000,000 properties around the world.
Why should I purchase my Winsted vacation bundle with Travelocity?
The three S's — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.
Can I save on my Winsted car rental if I combine it with hotels and flights?
Booking a Winsted vacation package with Travelocity is one of the best ways to save cold, hard cash. Bundle a car, hotel and flight, or any combination of them, and get access to great discounts. You could also throw in experiences and activities. After you've picked up the keys to the rental car, head out of the neighborhood and find out what the surrounding area has to offer. Around 95 mi from Winsted, Times Square is worth a road trip.
What is there to do in Winsted?
Highland Lake and Laurel Lanes are popular with so many visitors. Cross these sights off your must-see list and discover what the hype is about.

Photos of local treasures

Browse Winsted vacation photos for more inspiration

A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.
A brick building with green shutters, a white door, and a brick entrance.
A tractor with large tires and a red frame, parked next to a birch tree in a forested area with autumn-colored foliage.