Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
About this house rental
Nestled in Winchester, this lovely house for $231 per night is a great choice for your next vacation. RATE NOTE: Email for reduced on rate for off-season visits for more than 6 nights (November through April) . Antique but fully modernized cottage, located among the very best of locations at Highland Lake. If you are aesthetically minded, if you are looking for something particularly charming and special, you will love this Victorian era waterfront cottage totally restored from the ground up in 2016. If you are seeking a very nice spot on the lake, you will love this property. Canoe, Kayak, Sunfish Sailboat, and more to enjoy. If you have rented cottages before, you know that location on the lake makes a difference. Our cottage is located on the favored east side of the lake, with best sunshine. It is located away from the boat traffic and boat wake waves, on a quiet cove open to the largest of the lakes bays. Nice swimming area for kids. It has the important things experienced visitors to our lake recognize. It is a Victorian beauty, but fully restored in 2016 to high standards. Toasty warm in winter with lower level radiant heated floor, air conditioned for summer. Fully equipped kitchen, open-concept. We re-purposed original and vintage materials for this loved Victorian era cottage during our restoration. Every window and door has a story. Just ask us! Easy to use gas fireplace. Great for crisp mornings. Bedrooms include: one queen, one full and 2 bunks. Wake up in the queen and full bedrooms to sunrise on the lake. Spectacular views. Also upstairs, is a comfortable reading area and desk, a full bathroom with a 2 person, fully tiled shower, while the downstairs bath boasts a sparkling, new claw foot soaking tub. Downstairs, you will find a fully equipped kitchen, full-sized fridge, dual-fuel stove (gas stove top/electric oven), dishwasher and apron farm sink. Guests can dine on the old world dining table and Hitchcock chairs made locally, or at the kitchen peninsula. We have an open concept kitchen/dining/living room area which opens, through french doors, onto a large deck, just steps from the lake front. Enjoy the gas grill and picnic table for afternoon BBQs or glowing white lights and sunsets for a lovely evening dinner party. Bring your boat or jetski and tie up at our lakefront dock. This lake is great for swimming, boating, water-skiing and fishing. Private lawn and water front. Sunny side of the lake. The cottage is close to 'the Secret Spot,' (shallow area great for small children to play in the water). We live next door to the cottage. Our boat is parked on the south side of the dock in front of our place, your boat, if you bring one, is docked on the right north side directly in front of your cottage. Our area offers wonderful restaurants and grocers using locally produced food, Farmer's Markets (don't miss Litchfield's Saturday Farmer's Market!), the Gilson Cinema/Cafe, Antiquing, nearby fly-fishing, hiking, and biking. Stop in at a local farm for just picked corn or tomatoes, or an after dinner ice-cream cone. For anyone up for a Berkshires experience, we are less than a one hour, country drive from Tanglewood, Shakespeare and Co., Stockbridge, Great Barrington, Lenox, and the Outlets at Lenox. During the summer, we request a minimum 7 day booking, Saturday to Saturday. Also, we cannot accommodate pets, due to potential allergies of renters. However, there is a highly respected kennel close to the other side of the lake. Of course, it's great in the summer, but fall and winter offer their own special activities. Fall leaves, apple picking, hay rides and pumpkin patches in the country. Winter snow, skiing, flannel sheets and cozy fires. Our cottage can comfortably accommodate all seasons!
Amenities
Air conditioner
Kitchen / Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony / Patio
Dishwasher
TV
Garden
Family friendly
Map of Winchester, CT
Reviews
5.0/5.0
Outstanding(46 Reviews)
5.0
This property could not have been better. It was clean as could be and set up to be very comfortable. The kitchen is complete for all your cooking needs. The views of the lake were stunning.
We have stayed in VRBOs in the States and Europe and of all of them John is the best host so far. He saw to our every need without hesitation and then some. He is a cool dude.
We will stay here again!
Thank you John, you rock.
5.0
All excellent -- waterfront, layout, kitchen, host, feel, area! Really nice. Mattresses are on the firm side.
5.0
Clean, cute and cozy. As advertised. Only drawbacks were the weather and fish weren’t biting.
5.0
My sister and our two cousins rented this cottage for the week and thoroughly enjoyed it. House was very clean and lovely. Kayaking and hiking were on the to do list and was great fun. We would all highly recommend a stay here.
5.0
Relaxing
My sister and our two cousins rented this cottage for the week and thoroughly enjoyed it. House was very clean and lovely. Kayaking and hiking were on the to do list and was great fun. We would all highly recommend a stay here.
5.0
Great care went into the update of this home, it is full of charm and all the conveniences of home and sits on a very clean lake! Waking up to the beautiful lake views from the two front bedrooms starts your day off right! The dock provides access to the water with walk-in steps making it easy for both adults and children. We enjoyed the canoe, kayaks and the host was very gracious and gave my family a tour of the lake in his motorboat. We spent many hours on the large front deck, having coffee in the morning and diner in the evening. If you are looking for the lake experience of relaxation and plenty of water activities this is it! Thank you for a wonderful stay!!
5.0
This is our sixth year vacationing on a lake in New England with my family. The accommodations were lovely and the lake was pristine. It was a perfect location for my grandchildren (ages 4 & 5). Both were tearful when it was time to leave. Although we spent much of our time in the water, the area had a lot to offer. The owners could not have been more accommodating. This was definitely a vacation to remember and we hope to return.
5.0
Looking for a lake house experience? Look no further.
Great care went into the update of this home, it is full of charm and all the conveniences of home and sits on a very clean lake! Waking up to the beautiful lake views from the two front bedrooms starts your day off right! The dock provides access to the water with walk-in steps making it easy for both adults and children. We enjoyed the canoe, kayaks and the host was very gracious and gave my family a tour of the lake in his motorboat. We spent many hours on the large front deck, having coffee in the morning and diner in the evening. If you are looking for the lake experience of relaxation and plenty of water activities this is it! Thank you for a wonderful stay!!
5.0
Summer Vacation
This is our sixth year vacationing on a lake in New England with my family. The accommodations were lovely and the lake was pristine. It was a perfect location for my grandchildren (ages 4 & 5). Both were tearful when it was time to leave. Although we spent much of our time in the water, the area had a lot to offer. The owners could not have been more accommodating. This was definitely a vacation to remember and we hope to return.
5.0
We had a blast. Peace and quiet when we needed it. And fun in the sun when we wanted it! This lakefront property had it all! Looking forward to next year!!!
5.0
Wonderful experience
We had a blast. Peace and quiet when we needed it. And fun in the sun when we wanted it! This lakefront property had it all! Looking forward to next year!!!
5.0
Excellent rental experience. Loved the property, the large deck, full kitchen and grill. The lake was clean and refreshing, we enjoyed boating and swimming each day. Friendly and helpful owners/neighbors. Would love to return.
5.0
Beautiful lake house
Excellent rental experience. Loved the property, the large deck, full kitchen and grill. The lake was clean and refreshing, we enjoyed boating and swimming each day. Friendly and helpful owners/neighbors. Would love to return.
5.0
Lovely, peaceful, charming. Beautiful view. Very nice owners.
5.0
Lakeside idyll
Lovely, peaceful, charming. Beautiful view. Very nice owners.
5.0
We so appreciated our stay! The home and deck were amazing! Everything we needed was in the home, check in was easy, great communication, clean, cozy with many nice touches!
5.0
Beauty on the lake!
We so appreciated our stay! The home and deck were amazing! Everything we needed was in the home, check in was easy, great communication, clean, cozy with many nice touches!
5.0
Relaxing weekend at the lake
We had a great time relaxing at this cute lake house! It was the perfect size for me, my husband and 8 month old son and we enjoyed spending time on the deck looking at the water. We would definitely book again for a future trip especially once the little one gets older and he can enjoy the water more.
5.0
We had a great time at this lake rental. Jack was very responsive and set us up to go canoeing on the lake. The house was very cozy, with beautiful views. Would love to come back in the future!
5.0
Great week at the lake!
We had a great time at this lake rental. Jack was very responsive and set us up to go canoeing on the lake. The house was very cozy, with beautiful views. Would love to come back in the future!
5.0
Property was very clean. Property owner lives next door and is very friendly and helpful. He brought over a DVD player for the kids to watch a movie which was nice. Beautiful area.
5.0
Great Lakehouse
We had a wonderful long weekend at this incredible property. The lake house was immaculate. So cozy and charming. We loved spending time on the oversized deck taking in the beautiful views as well as a little "me" time in the spa like soaking tub. John was a wonderful host, extremely flexible and accommodating to ensure our weekend was perfect. Thank you for sharing your lake house.
5.0
Lovely Lakeside Home
We found everything to be as promised. All bedrooms are upstairs and there are stairs to the ground floor living room and kitchen. The kitchen has most everything you'd need and there is a grill outside. Furniture is comfortable and the gas powered fireplace make it comfy.
5.0
Nice lake house with character.
Property was very clean. Property owner lives next door and is very friendly and helpful. He brought over a DVD player for the kids to watch a movie which was nice. Beautiful area.
5.0
Quaint, sweetly furnished, cozy cabin right on Highland Lake. We wanted to enjoy the foliage and we had a wonderful time. The cottage is in close proximity to all the most charming towns in Litchfield county. Spectacular in autumn! Highly recommend.
5.0
Beautiful cottage
Quaint, sweetly furnished, cozy cabin right on Highland Lake. We wanted to enjoy the foliage and we had a wonderful time. The cottage is in close proximity to all the most charming towns in Litchfield county. Spectacular in autumn! Highly recommend.
5.0
Wonderful Relaxing Weekend
We really had a wonderful time at The Lone Pine Cottage. The property was immaculate. The house was stocked with everything you could possibly need to make your stay comfortable. Jack was a friendly and fantastic host! My husband and my two boys and I had a nice relaxing weekend which is what we needed. Next time we hope to stay longer. The soaking tub was amazing and the woodburning stove was cozy and warm. The views of the lake and the fall foliage was beautiful and we created memories that will last a lifetime.
5.0
My husband and I spent 3 nights at this beautifully restored lakeside cottage. The house was super clean and well equipped. The weather did not cooperate so we did not spend as much time paddling on the lake as we had wished.However the lake view from the beautiful cottage windows was so pretty.We were treated to a sightseeing ride around the lake in our host John’s boat which was so thoughtful.Hoping to plan another getaway in the future to this lovely cottage.Thank you for sharing it with us!Mary and Jim
5.0
Lovely Lakeside Location
My husband and I spent 3 nights at this beautifully restored lakeside cottage. The house was super clean and well equipped. The weather did not cooperate so we did not spend as much time paddling on the lake as we had wished.
However the lake view from the beautiful cottage windows was so pretty.
We were treated to a sightseeing ride around the lake in our host John’s boat which was so thoughtful.
Hoping to plan another getaway in the future
to this lovely cottage.
Thank you for sharing it with us!
Mary and Jim
5.0
Cute, super clean cottage with a beautiful spot on the lake. Kayaks and fire pit were great fun. Hosts, John and Jeaneena, are very attentive and respond quickly to emails. The queen bed is very soft so for those of you that prefer a harder mattress the twin bed is firmer.
5.0
Relaxing gem!
Cute, super clean cottage with a beautiful spot on the lake. Kayaks and fire pit were great fun. Hosts, John and Jeaneena, are very attentive and respond quickly to emails. The queen bed is very soft so for those of you that prefer a harder mattress the twin bed is firmer.
5.0
Great Weekend
This cottage is so lovely. We had such a relaxing and fun time. Beautiful, thoughtful details everywhere. We will definitely be back. Thanks for a great weekend!
5.0
This Property is Gorgeous!
The home is filled with all the comforts of home and more. The soaking tub could not be a better spot to relieve the pressures of the outside world and destress.
The area on this gorgeous, spring fed lake is perfect. It is very quiet and has limited boat traffic. At night all you hear is the sound of crickets.
Once you arrive you never want to leave. I will be back!
5.0
The home is filled with all the comforts of home and more. The soaking tub could not be a better spot to relieve the pressures of the outside world and destress.The area on this gorgeous, spring fed lake is perfect. It is very quiet and has limited boat traffic. At night all you hear is the sound of crickets.Once you arrive you never want to leave. I will be back!
5.0
Outstanding lake vacation
From the moment we stepped into the house we knew the experience would be wonderful and it certainly met and exceeded all expectations.
This house had everything we needed to enjoy the week. Truly a home away from home. The location on the lake is perfect. You get your own cove to swim in the clean and clear water. We called it our own natural pool. Easy access with stairs directly in.
Do not hesitate to book this gem.
5.0
Fantastic Lake Cottage
This property is beautiful, the location is perfect for a relaxing stay. The lake is great for swimming, boating and fishing and just to look at. Jack, the owner is great to work with and is very accommodating. He even provided assistance with putting my boat in the water and stowing the trailer during my visit.
5.0
Highly recommended!
A beautiful cottage: blissful deck overlooking the water!
5.0
Great house!
Had a fantastic time at this house on HIghland Lake. The owner even took the granddaughters out for a tour of the lake and gave them a boat driving lesson which they loved. Location and accomodations couldn't have been better.
5.0
Absolutely perfect for us.
Exactly what we wanted for a lakeside vacation. John is a great host! The cottage is beautiful, and it’s obvious there was a lot of thought and care put into renovating the cottage. Thank you for sharing your slice of heaven with us!
5.0
Amazing view, large deck, great sized cottage
We loved our 3-day staff at the Lone Pine cottage just before Christmas 2018. The deck is a great size and even though it's winter, we loved standing out there watching the ice on the lake and the fog roll through after the rain.The cottage is a great size and the gas fireplace in the main living area keeps it warm and cozy. The lake is beautiful; really nice taking a drive around looking at the houses! Great location, central to Main St and other places. Thanks for a lovely stay!
FAQs
How much does this house cost compared to others in Winchester?
The average price for a rental in Winchester is $200 per night. This rental is $31 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air?
We found 11 amenities for this rental. This includes air conditioner, kitchen / kitchenette, internet / wifi, fireplace, and parking.
Explore similar vacation rentals in Winchester
Explore all rentals in WinchesterWinchester travel inspiration
Read our blogGuides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023
Featured Rentals
Architectural Vacation Rentals: Experience the Beauty of Unique Properties
Featured Rentals
Sustainable and Eco-Friendly Vacation Rentals Around the World
Featured Rentals
Our Favorite Vacation Rentals With Unique Experiences
Featured Rentals
Amazing Cabin Rentals Across the Globe
Featured Rentals
Have You Ever Wanted to Stay in a Dome Rental? Now You Can
Featured Rentals
Jaw Dropping Treehouse Rentals All Over the World
Keep exploring
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals