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Our top choices for Winchester vacation rentals
1. Las Flores Villa
Las Flores Villa5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
The price is NT$29,401
NT$29,401
NT$46,944 total
includes taxes & fees
Nov 7 - Nov 8
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.
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.
Find vacation rentals that suit your style
Top Winchester Hotel Reviews
Blackberry River Inn
Blackberry River InnNorfolk
10/10 Excellent
Nice room, great location, excellent breakfast and infinitely helpful staff. Highly recommended.
Nice room, great location, excellent breakfast and infinitely helpful staff. Highly recommended.
Brandon
The White Hart
The White HartSalisbury
10/10 Excellent
We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches.
We were also able to park right outside our...
We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches.
We were also able to park right outside our...
thomas
The Abner Hotel
The Abner HotelLitchfield Historic District
10/10 Excellent
I was impressed by the historic charm of the hotel. There is even a dedicated room detailing the history of the area, educational significance and courthouse beginnings. The court room restaurant and rooftop bar are definitely worth a visit. The rooms were spacious and clean. We will definitely be back.
I was impressed by the historic charm of the hotel. There is even a dedicated room detailing the history of the area, educational significance and courthouse beginnings. The court room restaurant and rooftop bar are definitely worth a visit. The rooms were spacious and clean. We will definitely be back.
Karen
The Litchfield Inn
The Litchfield InnLitchfield
10/10 Excellent
Clean and charming , great atmosphere staff I great
Clean and charming , great atmosphere staff I great
Anonymous traveler
Home2 Suites by Hilton Bristol
Home2 Suites by Hilton BristolBristol
10/10 Excellent
great place
great place
Michelle
Simsbury 1820 House
Simsbury 1820 HouseSimsbury Center
10/10 Excellent
From the moment I arrived I knew my stay would be peaceful and comfortable. This is not a corporate, antiseptic hotel that could sit anywhere, this is a home.
The welcome is appreciated after a long day.
From the moment I arrived I knew my stay would be peaceful and comfortable. This is not a corporate, antiseptic hotel that could sit anywhere, this is a home.
The welcome is appreciated after a long day.
Warren
Residence Inn by Marriott Hartford Avon
Residence Inn by Marriott Hartford AvonAvon
10/10 Excellent
It was immaculate and every need anticipated. The staff was beyond friendly and they were not only knowledgable, but efficient. Highly recommend this hotel.
It was immaculate and every need anticipated. The staff was beyond friendly and they were not only knowledgable, but efficient. Highly recommend this hotel.
Anonymous traveler
Days Inn by Wyndham Torrington
Days Inn by Wyndham TorringtonTorrington
10/10 Excellent
The staff were very welcoming and friendly. It’s an older hotel but it’s clean and comfortable and very convenient location.
The staff were very welcoming and friendly. It’s an older hotel but it’s clean and comfortable and very convenient location.
Allen
Sheraton Hartford Hotel at Bradley Airport
Sheraton Hartford Hotel at Bradley AirportWindsor Locks
10/10 Excellent
Makes flights so much easier
Makes flights so much easier
Kimberly
Wilder House Berkshires
Wilder House BerkshiresSheffield
10/10 Excellent
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Clean, cozy, and charming. The breakfast is delicious and all went smoothly.
Liliana
Delamar West Hartford
Delamar West HartfordWest Hartford
10/10 Excellent
Beautiful warm yet modern design - ripe for Architectural Digest. Staff is friendly and helpful. Rooms are spacious and well-appointed. Morning breakfast is terrific. Cute town to navigate within steps of the hotel.
Beautiful warm yet modern design - ripe for Architectural Digest. Staff is friendly and helpful. Rooms are spacious and well-appointed. Morning breakfast is terrific. Cute town to navigate within steps of the hotel.
elizabeth
Truman Gillet House Bed & Breakfast
Truman Gillet House Bed & BreakfastGranby
10/10 Excellent
We came to see a local nursery and really enjoyed the hospitality, food, home comforts and EV charge-up. Wayne and Kim really know the area and are great guides. Plus the home is beautiful with a lovely yard to relax in.
We came to see a local nursery and really enjoyed the hospitality, food, home comforts and EV charge-up. Wayne and Kim really know the area and are great guides. Plus the home is beautiful with a lovely yard to relax in.
Christine
Belden House & Mews
Belden House & MewsLitchfield Historic District
10/10 Excellent
The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far.
The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far.
Anthony
The Old Inn On The Green
The Old Inn On The GreenGreat Barrington
10/10 Excellent
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Rishi
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLCEast Canaan
10/10 Excellent
Fantastic! Great service and friendly atmosphere. I would highly recommend Locust Tree Bed and Breakfast to all travelers!
Fantastic! Great service and friendly atmosphere. I would highly recommend Locust Tree Bed and Breakfast to all travelers!
rose
Hampton Inn & Suites Hartford/Farmington
Hampton Inn & Suites Hartford/FarmingtonFarmington
10/10 Excellent
Their service was impeccable, needed a few items and they delivered it within minutes to our room. They served a hot breakfast with plenty of choices, such a pleasant way to start our day. Plenty of towels at the pool, every moment was relaxing and stress free.
Their service was impeccable, needed a few items and they delivered it within minutes to our room. They served a hot breakfast with plenty of choices, such a pleasant way to start our day. Plenty of towels at the pool, every moment was relaxing and stress free.
Debora D.
DoubleTree by Hilton Hotel Bristol, Connecticut
DoubleTree by Hilton Hotel Bristol, ConnecticutBristol
10/10 Excellent
The hotel staff very nice, the pool very relaxing, the food was excellent. I will be back.
The hotel staff very nice, the pool very relaxing, the food was excellent. I will be back.
Susan
The Farmington Inn & Suites
The Farmington Inn & SuitesFarmington
10/10 Excellent
staff and breakfast excellent
staff and breakfast excellent
Wendy
Find out more about Winchester
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Frequently Asked Questions
Are there vacation rentals in Winchester?
Yes, there are vacation rentals in Winchester close to Laurel Lanes, or you can choose a more remote option if you're looking for extra privacy while you relax.
How many vacation rentals will I find in Winchester?
Expedia has 11 vacation rentals for your stay in Winchester.
What’s there to see and do in Winchester?
Highland Lake and Walker Field are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Laurel Lanes. While here, The Marina at Highland Lake and Burr Pond State Park are other places worth a visit.
What’s a vacation rental in Winchester like?
A vacation rental is a private property where you can stay for a few weeks or just a few days in Winchester. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.