Winsted Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Photo by Kim Knox Beckius
Choose two or more items and save on your trip:

Top Hotel Deals

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
32.23 km from city center
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport Windsor Locks CT
30.99 km from city center
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
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
32.31 km from city center
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd Avon CT
23.85 km from city center
Book a stay at this family-friendly hotel in Avon. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
16 Ella T. Grasso Turnpike Windsor Locks CT
31.89 km from city center
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant ...
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
29.04 km from city center
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, room service, and a health club. Our guests praise the helpful staff and the ...
Hampton Inn & Suites Hartford/Farmington

Hampton Inn & Suites Hartford/Farmington

2.5 out of 5
301 Colt Hwy Farmington CT
31.22 km from city center
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Delamar West Hartford

Delamar West Hartford

4 out of 5
1 Memorial Road West Hartford CT
32.07 km from city center
Book a stay at this spa hotel in West Hartford. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
2168 Poquonock Ave Windsor CT
31.89 km from city center
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Springhill Suites Marriott Airport

Springhill Suites Marriott Airport

3 out of 5
225 Ella Grasso Tpke Windsor Locks CT
32.25 km from city center
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff ...
DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut

4 out of 5
42 Century Dr Bristol CT
32.23 km from city center
Stay at this hotel in Bristol. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
2 Farm Glen Blvd Farmington CT
30.28 km from city center
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
2 Southampton Rd Westfield MA
36.34 km from city center
Book a stay at this business-friendly hotel in Westfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
21.98 km from city center
Book a stay at this business-friendly B&B in Simsbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Residence Inn by Marriott Hartford Avon

Residence Inn by Marriott Hartford Avon

3 out of 5
55 Simsbury Rd Avon CT
22.44 km from city center
Book a stay at this golf hotel in Avon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Dec 25 - Sun, Jan 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$93 Roundtrip, found 6 days ago
$93
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Dec 25 from Orlando Intl. to Bradley Intl., returning Sun, Jan 4, priced at $93 found 6 days ago
JetBlue Airways
Wed, Dec 24 - Wed, Dec 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Dec 24 from Orlando Intl. to Bradley Intl., returning Wed, Dec 31, priced at $143 found 6 days ago
American Airlines
Mon, Jan 12 - Sat, Jan 17
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Jan 12 from Ronald Reagan Washington National to Bradley Intl., returning Sat, Jan 17, priced at $199 found 3 days ago
Delta
Tue, Jan 13 - Sun, Jan 18
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jan 13 from Ronald Reagan Washington National to Bradley Intl., returning Sun, Jan 18, priced at $209 found 3 days ago
Breeze Airways
Tue, Dec 23 - Fri, Jan 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Dec 23 from Orlando Intl. to Bradley Intl., returning Fri, Jan 2, priced at $217 found 6 days ago