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Vacation Homes in Winsted

Our top choices for Winsted vacation homes

Private Room/Sunny/Clean/Peace/SelfCheckIn

2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay, would definitely highly recommend "
The price is SAR 540
SAR 700 total
includes taxes & fees
31 Aug - 1 Sep
Private Room/Sunny/Clean/Peace/SelfCheckIn

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is SAR 608
SAR 1,471 total
includes taxes & fees
3 Sep - 4 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

KING BED, Affordable Classic Bristol Home Sleep 8+

KING BED, Affordable Classic Bristol Home Sleep 8+

The Jefferson Guest House, Spacious, Special Views

10.0 out of 10, Exceptional, (6)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
The price is SAR 938
SAR 1,227 total
includes taxes & fees
31 Aug - 1 Sep
The Jefferson Guest House, Spacious, Special Views

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (4)
"The property was great and the house was huge even for all 12 of us "
The price is SAR 775
SAR 2,895 total
includes taxes & fees
1 Sep - 2 Sep
CT Gate House Goshen CT, Gate House Goshen CT

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is SAR 625
SAR 1,037 total
includes taxes & fees
3 Sep - 4 Sep
Home in Great Barrington

#21 *COMFORT & LUXURY*

8.0 out of 10, Very Good, (3)
"Highly recommend staying at this home! We had an excellent stay! "
#21 *COMFORT & LUXURY*

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.6 out of 10, Exceptional, (8)
"My boyfriend and I loved our stay at the cottage. Nicole was very easy to communicate with. The house was cozy and had everything we needed. Even though it rained all weekend, the hot tub and games made up for it. Thank you, Nicole! Can't wait to come back!"
The price is SAR 601
SAR 1,451 total
includes taxes & fees
3 Sep - 4 Sep
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

10.0 out of 10, Exceptional, (1)
"Smooth and straightforward check-in process. They were accommodating to our schedule and communicated everything in a timely manner. House was clean and everything looked as listed. Kitchen was well stocked with up to date appliances and plenty of utensils which was a nice surprise. Plenty of space for 7 of us, would suggest bringing an air mattress though if with a larger party. Overwhelming positive experience overall. "
The price is SAR 1,021
SAR 1,879 total
includes taxes & fees
31 Aug - 1 Sep
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

Premium 3-Story Townhome | Perfect for Large Groups

2.0 star property
9.2 out of 10, Wonderful, (5)
"Property as advertised & convenient - nice location. Great communication; appreciate the hospitality! "
The price is SAR 908
SAR 2,359 total
includes taxes & fees
10 Sep - 11 Sep
Premium 3-Story Townhome | Perfect for Large Groups

Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

9.4 out of 10, Exceptional, (6)
"Beautiful new spacious property in a great safe neighborhood. Very nice for groups. Common Living space s conducive for gathering. Property still under construction as there were other homes still being built. Near busy street but monimal noise. Would stay again."
The price is SAR 817
SAR 2,329 total
includes taxes & fees
1 Sep - 2 Sep
Massive 5 Bedrooms: 3King 2Queen, 10 mins to Downtown Hartford

Old Avon Village

2.0 star property
5.8 out of 10, (9)
"Very convenient location. Spacious and comfortable. Will definitely book again."
The price is SAR 435
SAR 1,301 total
includes taxes & fees
5 Sep - 6 Sep
Old Avon Village

Tranquil Litchfield Connecticut Retreat".

9.4 out of 10, Exceptional, (17)
"Good communication from the host"
The price is SAR 844
SAR 1,199 total
includes taxes & fees
3 Sep - 4 Sep
Tranquil Litchfield Connecticut Retreat".

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (2)
"Beautiful property and great location. A true retreat. "
The price is SAR 1,501
SAR 2,670 total
includes taxes & fees
31 Aug - 1 Sep
Charming Retreat at Stone Hill Estate – Nature Meets Luxury

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

10.0 out of 10, Exceptional, (59)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is SAR 976
SAR 1,705 total
includes taxes & fees
31 Aug - 1 Sep
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is SAR 889
SAR 1,886 total
includes taxes & fees
9 Sep - 10 Sep
Cheerful 3-bedroom cottage with woodstove

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

10.0 out of 10, Exceptional, (3)
"Great weekend with friends!"
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 10

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is SAR 750
SAR 1,376 total
includes taxes & fees
1 Sep - 2 Sep
Big farmhouse in the foothills of the Berkshires
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.
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Top Winsted Hotel Reviews