Winchester Lake Rentals | Vacation Rentals | Long Term Rentals
Beautiful lakefront home with views offers a relaxing close to nature getaway
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3 Bedrooms, 1.5 Bathrooms, Sleeps 6
Cottage in Winchester, CT
From $164.29 nightly weekday
Zip code 06094 is 0.8 miles from Winchester Lake
Renovated 3 bedroom, lake house with direct waterfront in the Litchfield hills on picturesque 76 acre Park Pond. Lounge and dine on the 2 tiered deck, fish off the large dock, swim and boat in the summer, snowshoe skate and ice fish in the winter....
Pristine Two Home Estate w/ Indoor Pool & Spa - Sleeps 30!
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14 Bedrooms, 9 Bathrooms, Sleeps 33
Estate in Norfolk, CT
From $2000 nightly weekday
Zip code 06058 is 3.1 miles from Winchester Lake
Roughland Estate, with two fabulous homes and 30 acres acres offers a larger group traveling together ease and luxury will being easily accommodated! The Estate House, originally the 200+ year-old-barn, it is now an ultimate world class home ava...
Historic Ice House At Highland Lake In Winsted!
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2 Bedrooms, 1 Bathrooms, Sleeps 6
House in Winchester, CT
From $150 nightly weekday
Zip code 06098 is 3.9 miles from Winchester Lake
This is a very unique property. It is a converted ice house (originally built in 1840s and converted in 1940s) complete with thick oak-paneled walls, fieldstone fireplace and lofts. It sits on an acre of wooded property and is very private. It ...
Waterfront Cottage Highland Lake-Litchfield Hills swimming fishing kyaking sail
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3 Bedrooms, 1 Bathrooms, Sleeps 6
House in Winchester, CT
From $135.71 nightly weekday
Zip code 06098 is 3.9 miles from Winchester Lake
Litchfield County - Highland Lake three-bedroom lakefront cottage with private dock. Located on the east side of lake -enjoy beautiful sunsets right on your private dock. Beautiful, clean lake 3.5 miles long. Trophy trout lake. Great bass fishing...
Enjoy lakefront living on pristine, spring fed Highland Lake.
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5 Bedrooms, 4 Bathrooms, Sleeps 12
House in Winchester, CT
From $816.67 weekly
Zip code 06098 is 3.9 miles from Winchester Lake
This recently constructed 5 BR/3 full baths, 2 half baths Highland Lakefront home boasts two master suites, both with spectacular lake views. The tiered yard with gently sloping beach make an ideal play spot for the very young and old alike. This ...
Beautiful, Spacious Hilltop Home. 7 Acres, Breathtaking Views.
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4 Bedrooms, 3 Bathrooms, Sleeps 8
House in Torrington, CT
From $400 nightly weekday
Zip code 06790 is 4.9 miles from Winchester Lake
This airy, light home is situated on a hill-top with panoramic views of farms and forested hills. The expansive home features a huge sun-room, dining room, and large living room, as well as a wide porch with views of the hills for enjoying morni...
Lakeridge Litchfield Resort Townhome Pool Tennis Skiing
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Townhome in Torrington, CT
From $1749.99 monthly
Zip code 06790 is 4.9 miles from Winchester Lake
**** Lakeridge on-site day camp registration has begun! Sports, Tennis, Horseback Riding camps available. Contact us for more information **** We are offering for rent a spacious 2 bedroom, sun-lit, 2-story, all-season townhome at the Lakeridge r...
5 BR LITCHFIELD Goshen CT WATERFRONT LAKE HOUSE with POOL
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5 Bedrooms, 4 Bathrooms, Sleeps 18
House in Goshen, CT
From $5500 weekly
Zip code 06756 is 6 miles from Winchester Lake
Our Contemporary lake house is on 2 waterfront acres on Woodridge Lake near the town of Litchfield, Bantam Lake, & Tyler lake. 5,200 sf waterfront home, 5 Bedrooms, 3.5 Baths, 3 Fireplaces, 2 Kitchens, large deck, expansive lake vistas from almos...
Beautifully Renovated House Overlooking Hollenbeck River
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3 Bedrooms, 3.5 Bathrooms, Sleeps 8
House in Falls Village, CT
From $400 nightly weekday
Zip code 06031 is 7.8 miles from Winchester Lake
As you turn into the driveway to this perfectly serene setting, any stress you may have will magically disappear. This special single level house sits next to a beautiful stream (actually the Hollenbeck River) on 3 quiet, peaceful acres in the nor...
Pristine New country home ,call for availably&rates
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4 Bedrooms, 3.5 Bathrooms, Sleeps 10
Chateau_/_country_house in Cornwall, CT
From $600 nightly weekday
Zip code 06796 is 9.6 miles from Winchester Lake
Built in 2013 Directly adjacent to Mohawk ski area!Charming and sophisticated Country home for the most discerning vacationer . Amazing views. Simplicity comfort and style all come together to assure a most enjoyable stay.The house has centra...
Magnificent Country Home, Litchfield, CT
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4 Bedrooms, 5.5 Bathrooms, Sleeps 8
House in Litchfield, CT
Zip code 06759 is 11 miles from Winchester Lake
For rent from November 1, 2012 to April 30, 2013: Located on 20+ acres off an exclusive road in Litchfield, CT this 9,000+ sq. ft. brick house features 4 bedrooms, 5 1/2 baths, very spacious rooms and wooden beams in the interior. This beaut...
1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
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5 Bedrooms, 4.5 Bathrooms, Sleeps 9
House in Litchfield, CT
From $275 nightly weekday
Zip code 06759 is 11 miles from Winchester Lake
This former tavern retains a lot of colonial-era charm and is a beautiful and peaceful place to stay. It remains a great home to entertain guests or to be by yourself to enjoy the solitude of the surrounding countryside. There is a Master Bedroom ...
New England Country Home in Village of Litchfield, Connecticut
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3 Bedrooms, 2 Bathrooms, Sleeps 7
House in LITCHFIELD, CT
Zip code 06759 is 11 miles from Winchester Lake
This serene, turn-key cottage is a quintessential New England property, located in the quaint village of Litchfield. The house sits on a private cul de sac, less than a mile from the town center, where one can easily walk to charming shops and re...
Indoor Pool, Sauna, Hot Tub, Jacuzzi & Solarium
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3 Bedrooms, 3 Bathrooms, Sleeps 7
House in Cornwall, CT
From $750 nightly weekday
Zip code 06754 is 13.3 miles from Winchester Lake
Prana Residence-Spa is a holistically designed residence provides total relaxation and the transformation of vital life (Prana). It is located on five and half acres atop the forested hills of Cornwall Bridge in Litchfield County, Connecticut, l...
Summer Lake Cottage, private beach, Berkshire Hills, small village
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5 Bedrooms, 3 Bathrooms, Sleeps 18
Cottage in Lakeville, CT
From $550 nightly weekday
Zip code 06039 is 13.9 miles from Winchester Lake
This is the lake cottage your grandmother visited during her childhood. Charming, original 1920 features. Big remodeled kitchen (new stove/oven) and big living room for family reunions and guests. Sleeps 9 in comfort; it has often slept 20. Porch...
Furnished 4 Bedroom Home In Center Of Lakeville 200 Feet From Town Beach
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4 Bedrooms, 2.5 Bathrooms, Sleeps 10
House in Lakeville, CT
From $225 nightly weekday
Zip code 06039 is 13.9 miles from Winchester Lake
This 4 bedroom, 3 bath house is fully furnished and available for short or long term rentals. The house has a new kitchen, air conditioning, cable TV and wireless internet. It is located approximately 200 feet from the entrance to the Town Grove w...
Charming Cottage on Lakeville Lake
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Cottage in Lakeville, CT
From $250 nightly weekday
Zip code 06039 is 13.9 miles from Winchester Lake
Please note: I will not be renting my home after Sept. 7, 2016 and this property description will no longer be viewable as of July 17, 2016. Adorable, renovated 2-level cottage (it's larger than it appears from the picture) with views of Lakevil...
Adirondack-Style/Alpine Cottage-beautiful Lake & Mountain Views-Peacefu
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2 Bedrooms, 1 Bathrooms, Sleeps 4
Cottage in Salisbury, CT
From $1495 weekly
Zip code 06068 is 14.4 miles from Winchester Lake
“ROARING BEAR” cabin is an alpine adronack style cabin originally built in 1922, situated on a pine forested hillside overlooking East Twin Lake- Lake Washining. It has a relaxed, attractive cabin decor featuring quality rugs, bedding, linens, qu...
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, Magestic Views
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2 Bedrooms, 1 Bathrooms, Sleeps 6
Cottage in Salisbury, CT
From $99 nightly weekday
Zip code 06068 is 14.4 miles from Winchester Lake
A charming lakefront cottage in the foothills of the beautiful Berkshire Mountains. Located on a peaceful lake with a private dock & shore-front with gorgeous lake & Mountain views. The cottage is only 50 feet from the lake and private dock. It co...
Peaceful, Secluded Brookside Home in Litchfield County
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3 Bedrooms, 1.5 Bathrooms, Sleeps 6
House in Sharon, CT
From $133.33 nightly weekday
Zip code 06069 is 14.7 miles from Winchester Lake
We call our wonderful vacation home, 'Serenity', because all your stress and worries will disappear when you're here! This beautifully renovated, 120 year-old former mill sits just feet away from a lovely brook on a 7-acre, heavily wooded lot jus...
'Ellsworth Cottage' for Rent in Sharon, CT
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3 Bedrooms, 2.5 Bathrooms, Sleeps 7
House in Sharon, CT
Zip code 06069 is 14.7 miles from Winchester Lake
Beautifully decorated & landscaped, 3 bedroom and 2 1/2 bath gem for rent on over 9 acres in Sharon, CT. Wonderful kitchen w/cozy window seat, working fireplace, and huge outdoor deck...perfect for entertaining. Huge master bath and 1 1/2 additi...
Modern Dwell-published home - available throughout the year
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3 Bedrooms, 2 Bathrooms, Sleeps 6
House in Sharon, CT
From $233.33 nightly weekday
Zip code 06069 is 14.7 miles from Winchester Lake
This is a perfect getaway on a quiet rural road, looking out on a private wooded view. The open entertaining area includes light-filled Living Room, Dining Room and Kitchen. The Kitchen has island seating and the cook looks over the garden - thi...
Secluded Country Setting W/Great Views,Chef's Kitchen,Wrapar Porch
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4 Bedrooms, 3 Bathrooms, Sleeps 13
Cabin in Sharon, CT
From $350 nightly weekday
Zip code 06069 is 14.7 miles from Winchester Lake
Enjoy the spectacular views of the surrounding Twin Oaks nature preserve on our wraparound mahogany porch in this 5 BR, 3Bath, adirondack-style country home. This lovely, secluded country retreat is just minutes from the MetroNorth station at Was...
Cozy 5 Bedroom Cottage on Bantam Lake
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5 Bedrooms, 2.5 Bathrooms, Sleeps 10
Cottage in Morris, CT
From $100 weekly
Zip code 06763 is 15.3 miles from Winchester Lake
Cute and cozy 5-bedroom lakefront furnished cottage with sunny deck, cottagey furnishings, beautiful sunsets, and your own private boat dock (shared with cottage owner) right out the back door. This is a sweet little spot that is perfect for fam...
Experience Perch Rocks! A Unique Private Waterfront Cottage on Bantam Lake
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2 Bedrooms, 1 Bathrooms, Sleeps 8
Cottage in Morris, CT
From $500 nightly weekday
Zip code 06763 is 15.3 miles from Winchester Lake
Perch Rocks is a luxury camp on Bantam Lake in Litchfield County! This is a true 'lake cottage' with classic shingle style. The cottage contains 2 bedrooms plus a loft, large kitchen, field-stone fireplace and covered front porch. Both bedrooms o...
Adirondack House on Lake Waramaug
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4 Bedrooms, 2 Bathrooms, Sleeps 8
House in New Preston, CT
From $475 nightly weekday
Zip code 06777 is 17.5 miles from Winchester Lake
If you are looking for a home away vacation that involves unlimited amount of rest and relaxation,swimming, boating, hiking, cycling, antiquing, award winning vineyards, terriffic restaurants from casual to formal,family fun & adventures, quaint N...
Enjoy the Hamptons of New England in a Renovated Barn,
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5 Bedrooms, 4 Bathrooms, Sleeps 11
Farmhouse in Kent, CT
From $3000 weekly
Zip code 06757 is 18.9 miles from Winchester Lake
A 4000 square foot country home in the heart of Northwest Connecticut. 2 hours from Manhattan and a 5 minute walk to the Kent Falls. 5 Bedrooms, 4 baths, an in ground pool, hot tub and all the comforts of home. 4 queen beds, 2 en suite Mast...
A Sophisticated and Intimate New England Country House
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5 Bedrooms, 3.5 Bathrooms, Sleeps 12
Estate in Washington Depot, CT
From $1270 nightly weekday
Zip code 06794 is 19.6 miles from Winchester Lake
Hidden Valley is a unique place. A sophisticated and intimate property overlooking a breathtaking nature preserve of the same name in the hills of Washington, Connecticut in Litchfield County. Hidden Valley's rooms include an exquisite semi-atta...
The Orange Gild Bed and Breakfast with private Spa, Washington CT
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2 Bedrooms, 2 Bathrooms, Sleeps 6
House in Washington, CT
From $350 nightly weekday
Zip code 06793 is 19.9 miles from Winchester Lake
Please contact us directly for better rates!!! g.o-o.g-l.e ORANGE GILD WASHINGTON CT This is a Bed and Breakfast and that means you do not get the whole house to yourself. However, privacy should not be an issue if you take both rooms because you...
Extraordinary Modern Home with Heated Gunite Pool & Spectacular Views
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4 Bedrooms, 3.5 Bathrooms, Sleeps 9
Chateau_/_country_house in South Kent, CT
From $5000 weekly
Zip code 06785 is 21.2 miles from Winchester Lake
Newly built country getaway with new 40' heated gunite saltwater pool and spa, eat-in chef's kitchen, vaulted great room with exposed beams, playroom, tv room and raised blue stone terrace for bug-free outdoor dining. Two separate oversize master...
Kent-Spectacular Panoramic View of Litchfield Hills- Private Lake for Boating
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4 Bedrooms, 4.5 Bathrooms, Sleeps 12
House in Kent, CT
From $24999.99 monthly
Zip code 06785 is 21.2 miles from Winchester Lake
Our home sits atop a ridge on a secluded gravel road. COMPLETE PRIVACY. Magnificent views await you from every room of the house for miles and miles of the Litchfield Hills. The house is part of a lake association, so you have a private lake to sp...
Beachfront home with direct lake access, private sandy beach
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3 Bedrooms, 2.5 Bathrooms, Sleeps 12
House in Suffield, CT
From $325 nightly weekday
Zip code 06093 is 22.4 miles from Winchester Lake
This home has a private dock. Feel free to bring your own motor boat, jet skis or kayaks for use on this private beachfront property. 3 bedrooms, 2 1/2 baths with all NEW furniture and mattresses. Bedroom 1=First floor, queen mattress Bedroom 2=S...
5BR Sept-May $5900/mo+Utilities,$1,950/wknd, $2450/wk, Summer $59K or $24,900/mo
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5 Bedrooms, 3 Bathrooms, Sleeps 10
Chateau_/_country_house in Roxbury, CT
From $975 nightly weekday
Zip code 06783 is 25.6 miles from Winchester Lake
If you are searching for the perfect country escape in a meticulously restored country home on scenic dirt road with a barn, stream, and pond, Roxbury Colonial is for you! The home features a stainless steel chef's kitchen, vaulted barn style liv...
Chalet Home at Candlewood Lake, Private Beach, Owner Managed.
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2 Bedrooms, 1 Bathrooms, Sleeps 6
House in New Milford, CT
From $110 nightly weekday
Zip code 06776 is 25.9 miles from Winchester Lake
Cozy chalet-style home in attractive, private Candlewood Lake community is perfect for a family vacation or a couples get-away. Beautiful private beach in desirable New Milford Bay with western exposure is complete with picnic tables, grills, swi...
Direct Water Front Home
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3 Bedrooms, 2 Bathrooms, Sleeps 6
House in New Milford, CT
From $525 nightly weekday
Zip code 06776 is 25.9 miles from Winchester Lake
Fully furnished direct waterfront single family home. 3 bedrooms, 2 full bathrooms, and living room with large stone fireplace. Lower level family room with sliders leading out to a fieldstone patio. Three decks, screened in porch and private dock...
Charming Beach House in Clinton-steps from sandy private beach-enclosed yard/
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3 Bedrooms, 1 Bathrooms, Sleeps 4
Cottage in Clinton, CT
From $899.99 weekly
Zip code 06103 is 26.6 miles from Winchester Lake
Charming beach house in lovely quiet area on Ct. shoreline - 2 houses away from 1 0f 2 private beaches - 3 bedrooms (sleeps 4) Air Conditioned - comfortable enclosed back porch with windows all around for cool breezes - private back yard...
Candlewood Lake Waterfront
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4 Bedrooms, 2 Bathrooms, Sleeps 9
House in Brookfield, CT
From $399 nightly weekday
Zip code 06804 is 32.7 miles from Winchester Lake
This private lake front home and dock which sleeps 9 offers you unparalleled enjoyment. Access to the private community white sands beach with large meadow area is a wonderful addition to your stay. Visit waterfalls, winery, hiking, and biking in ...
Eve's Country Retreat
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4 Bedrooms, 2.5 Bathrooms, Sleeps 10
House in Ellington, CT
From $128.57 nightly weekday
Zip code 06029 is 37.4 miles from Winchester Lake
Retreat to this peaceful and very spacious country home nestled in rolling Connecticut Valley farmlands within walking distance to the green, library, and 18th and 19th century historic homes of the town of Ellington (1786). Enjoy the serene inter...
Sea Watch - Ocean Front with Beach, Incredible Views!
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3 Bedrooms, 2 Bathrooms, Sleeps 6
House in Dennis Port, Ma
From $300 nightly weekday
Zip code 06232 is 41.9 miles from Winchester Lake
Sea Watch - Ocean Front with beach Incredible views! Pets OK. Our renovated 3 bed/2bath ocean front home has the charm of Old Cape Cod with all the benefits of the new to provide the perfect place to create your Cape Cod memories! You can bring ...
Coventry Lake / Wangumbaug Lake Waterfront with dock
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2 Bedrooms, 1 Bathrooms, Sleeps 5
Cottage in Coventry, CT
From $125 nightly weekday
Zip code 06238 is 43 miles from Winchester Lake
Beautiful waterfront house/cottage for rent with awesome views overlooking Coventry Lake and Underwood Island, there are a variety of activities and attractions always going and all kinds of activities from i.e.; boating, jet skiing, waterskiing, ...
Upstairs suite Two bedrooms One bathroom
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2 Bedrooms, 1 Bathrooms, Sleeps 4
House in Redding, CT
From $135 nightly weekday
Zip code 06896 is 43.5 miles from Winchester Lake
Private 2 bedroom suite in the upstairs of our quiet home in rural Redding CT. Park in our large off road driveway then walk in front door up private stairs to your 2nd floor suite. Beautiful views of wooded back yard from each room. In summer use...
Steps to beach, water views 3 sides; 15% discount for Aug. 5-12
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3 Bedrooms, 3 Bathrooms, Sleeps 8
House in Guilford Center, CT
From $600 nightly weekday
Zip code 06437 is 46 miles from Winchester Lake
This vacation property sits across the street from a 25 acre sandy beach/park/playground. This large, beautifully appointed, 2700 (+ basement game room) home was built in 2000 by the owner with loving care and attention to details. There are stun...
1930s Waterfront Cottage on Tuttles Point
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5 Bedrooms, 1 Bathrooms, Sleeps 8
Cottage in Guilford, CT
From $2300 weekly
Zip code 06437 is 46 miles from Winchester Lake
Remember 'doing the dishes' with family members and friends? Do you love an outdoor shower? Visit this charming 1930's summer cottage with direct water access, large screened porch with wonderful 180 degree views of Long Island Sound. Sleep in th...
Charming waterfront cottage with spectacular ocean views
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Cottage in Guilford, CT
From $1300 weekly
Zip code 06437 is 46 miles from Winchester Lake
Charming, shingled waterfront cottage for rent by week or month in historic Guilford, Connecticut. Swim and kayak from the front of the house; a beautiful, sandy, private beach is just steps away. House has 2 bedrooms and 2 full baths, plus an add...
Waterfront. Fully Refurbished in a Picturesque Town. 75 Miles from Nyc
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2 Bedrooms, 2 Bathrooms, Sleeps 8
Cottage in Guilford, CT
From $1000 weekly
Zip code 06437 is 46 miles from Winchester Lake
There's a video link it is at the bottom of the Amenities page below. Please note, Minimum stay 7 nights. Minimum stay 7 nights. Minimum stay 7 nights. The main house is a beach cottage with petite master bedroom, a kitchen with dishwasher,micr...
Private Island ! Thimble Islands, Bridge, Beach
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3 Bedrooms, 2 Bathrooms, Sleeps 8
House in Guilford, CT
From $450 nightly weekday
Zip code 06437 is 46 miles from Winchester Lake
This recent Nantucket Shingle Style Waterfront Home is located on NARROWS ISLAND in Long Island Sound. The island is part of the archipelago known as the Thimble Islands. It is the only island of the Thimbles with a bridge, making it accessible by...
Pine Orchard Contemporary Home on Large Lot with Beach Rights
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6 Bedrooms, 5 Bathrooms, Sleeps 11
House in Branford, CT
From $490 nightly weekday
Zip code 06405 is 46.8 miles from Winchester Lake
We now have a video of the property located in the Amenities Tab at the bottom UPDATE: Beginning September 1 2010 property will be available for long term rentals. Please inquire for long term details. Thanks. A Branford, CT Waterfront Commun...
ESTATE Vintage New England private point w/ beach + in-law apt.
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5 Bedrooms, 5 Bathrooms, Sleeps 12
House in Stony creek, Ct
From $7000 weekly
Zip code 06405 is 46.8 miles from Winchester Lake
The reflective, tranquil powers of water is unique -no where is this experience so spectacular than from the window of ones own space as you awaken . Vacation like a celebrity in designer appointed 5 bedroom home-touch football, volleyball ,badm...
Thimble Island Paradise (Branford, CT)
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5 Bedrooms, 2.5 Bathrooms, Sleeps 10
House in Branford, CT
From $500 nightly weekday
Zip code 06405 is 46.8 miles from Winchester Lake
A unique Victorian summer home accessible only by boat, on one of the larger Thimble Islands surrounded by Long Island Sound in quaint Stony Creek, town of Branford, CT. The front porch of the 1898 home offers panoramic sunsets to the west. The ...
ISLAND GETAWAY! June Availabilities
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3 Bedrooms, 2 Bathrooms, Sleeps 9
House in Branford, CT
From $3500 weekly
Zip code 06405 is 46.8 miles from Winchester Lake
Pot Rock Island ( AKA Treasure Island) The Thimble Islands, Stony Creek, Connecticut! Pot Rock Island is one of the 32 seasonally inhabited Thimble Islands, carved by the glacier then strung like pearls and cast onto Long Island Sound off the c...
     

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