Winchester, CT
Travel Guide
Visit Winchester
The Farmington Inn & Suites
827 Farmington Ave Farmington CT
$144 nightly
The price is $166 total per night from Jul 12 to Jul 13
$166 total
Jul 12 - Jul 13
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,004 reviews)
"The stay at Farmington Inn met all of our needs and expectations. A great place to stay and relax."
Reviewed on Jul 9, 2026
Avon Old Farms Hotel
279 Avon Mountain Rd Avon CT
$178 nightly
The price is $205 total per night from Jul 14 to Jul 15
$205 total
Jul 14 - Jul 15
Total with taxes and fees
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 ...
8.4/10 Very Good! (1,016 reviews)
"Outdoor pool setting was so pretty under the pines! Rooms could use updating, when the ac wasn’t set to 65 the room got very musty smelling."
Reviewed on Jul 11, 2026
Delamar West Hartford
1 Memorial Road West Hartford CT
Fully refundable
$392 nightly
The price is $448 total per night from Jul 26 to Jul 27
$448 total
Jul 26 - Jul 27
Total with taxes and fees
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 ...
9.8/10 Exceptional! (1,003 reviews)
"Loved how clean the hotel was. The AC and fresh quality of the room. Staff very friendly. The restaurant lowered the quality tremendously. It didn’t match. Although breakfast was included the quality was watered down. Same buffet every morning. Taste was lower grade. Presentation looks good but the ..."
Reviewed on Jul 6, 2026
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.
Private Island - Largest Fresh Water Reservoir in Mass
Otis MA
Stay at this cottage in Otis. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Larkum Pond and Otis Reservoir are located nearby.
8.6/10 Excellent! (9 reviews)
"Location was wonderful, panoramic lake view.Glassed in porch was the primo spot to just relax and chill. Main bedroom and living room were good size. Kitchen was well appointed except for one staple item, no microwave! Second bedroom and bathroom are very small. You’ll want to bring your own linens, ..."
Reviewed on Oct 14, 2025
Lakefront Summer Stunner in New England Just 2 Hours From NYC
Sharon CT
Stay at this vacation home in Sharon. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Indian Lake and Veterans Field are located ...
10/10 Exceptional! (94 reviews)
"This litle house on the lake was the perfect getaway from the hubub of daily life. Situated in a peaceful and picturesque locale, the house is small but well appointed, with a full updated kitchen and a nice updated bathroom. We had trouble making the same-day booking, and Amanda (the owner) went ..."
Reviewed on Jul 9, 2026
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield MA
Stay at this cabin in Sandisfield. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Lake Garfield and Otis Ridge are located ...
9.6/10 Exceptional! (52 reviews)
"Spacious house; huge lot with a tennis court"
Reviewed on Jun 8, 2026
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 Winchester attractions
- Winchester Historical Society
- Lake Compounce
- Lime Rock Park
- Elizabeth Park
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Ski Butternut
- Lake Waramaug State Park
- Taconic State Park
- Lake Waramaug
- New England Air Museum
- Harlem Valley Rail Trail
- Warner Theater
- Otis Reservoir
- The Christmas Shop
- Blue Back Square
