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Prospect Holiday Homes

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    Don't let other travellers get your favourite Prospect area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 30 Rentals in Prospect
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    The following rentals are within 30 kilometres of Prospect.
    Its the Perfect Weekend House just 80min from NYC!1 / 23
    (3)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Milford
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Beach House, Private Beaches, Casinos, Yale U1 / 19
    (10)Excellent
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    East Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hobbit House has been newly renovated and appointed to be cozy and comfortable with an antique flair. This property is beautiful inside and out. The beach use for this property is private and your rental of this property comes with everything you need to relax at the beach! This house has the...
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    East Haven, Connecticut 06512
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Roxbury
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Patio
    • Housekeeping Included
    • Washer
    • Central Heating
    • Balcony
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for families or reunions! We love small groups. Through Karina arrange a catered meal and relax from hustle and care. Soak up the history and beauty in a place that resonates with centuries of community and warmth. Beyond the pool, an ice house reminds us of life before electricity. A...
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    Roxbury, Connecticut 06783
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    Litchfield
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Washer
    • Parking
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish in the luxuries and comforts of this 3-bedroom, 2-bathroom vacation rental house in Litchfield! 'Stone-Peca' is a quintessential New England property that sits on a half acre of land and offers a spacious backyard with a deck and patio. Stylish, high-end decor adorns the interior, making...
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    Litchfield, Connecticut 06750
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bethlehem
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Judd Farm House is situated on 33 acres, the house is in farm country. It is surrounded by rolling hills of Litchfield. There are country roads for walking and biking with very little traffic. It is a perfect retreat for a group there are generous size bedrooms tastlefully decorated. There is a...
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    Bethlehem, Connecticut 06795
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Terrace
    • Balcony
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy life in an authentic 1900s New England seaside village when you stay in this gorgeous two-bedroom, one-bath home. This Morris Cove corporate housing property is just 10 minutes from downtown New Haven, which means you’re close to Yale Hospital train station, Yale University, and the airport....
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    New Haven, Connecticut 06512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Branford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Patio
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About this listing Direct waterfront cottage recently completely remodeled. Open concept floor plan with walls of windows facing water. Large deck on water makes it feel like you are on a boat. Walk to restaurants, ride a bike on scenic RT 146, fish, kayak or just walk the neighborhood. Enjoy all...
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    Branford, Connecticut 06405
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    East Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Parking
    • Ocean Views
    • Grill
    • Waterfront
    • Balcony
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated direct beach front house on private beach, beautifully furnished and detailed. All the comforts of home and more! Fully equipped new 'vintage reproduction' kitchen, washing machine and dryer, towels linens, beach chairs, outdoor stove in enclosed screened in porch and cooking area...
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    East Haven, Connecticut 06512
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is in a historic village with 22 others clustered around the Congregational Church across the street from the house. Built in 1795 it has four large corner rooms on both floors On the first floor there's a central entry hall, with dining and library to either side, straight ahead are...
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    Southbury, Connecticut 06488
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Middlefield
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Waterfront
    • Private Garden
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clarke's Landing is newly built 2 story lakefront house with heat and air conditioning! It is a family home and has all the amenities that you would have at home.Everything is NEW! It includes cable and WiFi internet, new quality linens, paper goods, shampoo,spices, beach towels, chairs , floats...
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    Middlefield, Connecticut 06455
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Quiet Getaway in Historic Village1 / 27
    (1)Excellent
    Southbury
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Secure Parking
    • Mountain Views
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 January 2015
    My husband and I, and our doggies, enjoyed the Coach House so much. We became friends with the owner who was very accomodating. He even loaned us his ornaments, so we could...
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    About this property
    Charming, recently renovated, two-story, 1,200 square-foot coach house built in 1795 and set in a tranquil 3-acres of lawns, gardens, orchards and forest at the heart of the historic Village of South Britain founded in 1715 by settlers from the south of England, This vacation home an hour and a...
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    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wallingford
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Terrace
    • Air Conditioning
    • Patio
    • Parking
    • Satellite TV
    • Internet Access
    • Porch
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to The Wallingford Victorian Inn We are a B&B The room rate posted is for one suite that will sleep 2 We have 5 suites available for rental if your party is larger The rate is per suite per night The Wallingford Victorian Inn regally presides over the corners of North Main Street and...
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    Wallingford, Connecticut 06492
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Middlefield
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful newly remodeled cottage is located on Lake Beseck in picturesque Middlefield, Ct. The views of the lake are serene and produce an immediate feeling of tranquility. This is a family home and has all the amenities that you need to feel at home including a complete kitchen. Betty's Boat...
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    Middlefield, Connecticut 06455
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best way to experience Roxbury Connecticut... A completely Private Apartment in Modern contemporary home located on Route 67 in Roxbury Connecticut. 2 Bedrooms, Full Kitchen, Full Bathroom, Living Room, Oversized Deck, Outdoor Grill, and 3+ Acres of Land with Outdoor Seating. Close to...
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    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Milford
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The first floor apartment is bright, sunny and airy. The beach is right across the street with unobstructed views of Charles Island. You can also walk right over to a seasonal Greek restaurant next door, or to Silver Sands State Park for more recreational activities. We are right next door if you...
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    Milford, Connecticut 06460
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ennis Cottage with private beach on Branford shore1 / 17
    (15)Excellent
    Branford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Satellite TV
    • Patio
    • Grill
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2016
    Thank you Ron and Bernie for making our vacation an excellent one. The rental house was compact, but with everything we needed, at hand. At the end of our vacation we didn't...
    Reviewed 11 July 2016
    The cottage was everything we expected and more!! Ron and Bernie were the friendliest of people and we could tell that they wanted our vacation to be the best. They are very...
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    About this property
    This newly renovated one bedroom cottage is set in the midst of other cottages. With a private back garden, patio, beautiful flowers, and steps from a private neighborhood beach , the cottage is clean, and comfortable. For cool nights there is a gas fire, and an air conditioner in the bedroom...
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    Branford, Connecticut 06410
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Bright, cheery contemporary ranch style home1 / 20
    (1)Excellent
    Cromwell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Washer
    • Secure Parking
    • Air Conditioning
    • Outdoor Dining Area
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2015
    I loved staying at this comfortable home. The area, Middletown CT is centrally located and the home,on Rolling Green is centrally located. It's about 20 minutes from everywhere...
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    About this property
    This house is bright and cheerful even during winter months due to the large paladian windows and cathedral ceilings.<BR>If you find that you are traveling to Connecticut for work assignment or vacation, consider this option to hotel living.<BR>Our home will welcome you from travel or work with...
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    Cromwell, Connecticut 06457
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hamden
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Patio
    • Grill
    • Air Conditioning
    • Secure Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Royal Master Suite offers the finest set of amenities similar to those found in any luxury resort. With plenty of room to live, breathe, read, or sleep in comfort, this boudoir is truly a treat. This Colonial Home has a warm, inviting atmosphere with a hostess who is knowledgeable about...
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    Hamden, Connecticut 06514
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, furnished, deluxe condo in the core of Portland, Oregon…with fantastic views of the West Hills, PSU, and Downtown Portland. The condo is just East of the Portland State University Campus. Rented on a month by month basis. Convenient to all aspects. Attributes: √ Near the top of the...
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    Portland, Connecticut 97201 2249
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
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    Bethlehem, Connecticut 06751
    Private Room - 5 Bedrooms, Sleeps 10
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    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magnificent, fully furnished 1st floor apartment of our 2 story home in one of the best areas of Seymour, CT. Our apartment is for non- smokers only. Very clean and calm. The apartment features a spacious living room with a 2 comfortable futon and one couch, a separate bedroom with queen size bed,...
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    Seymour, Connecticut 06483
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Meriden
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Satellite TV
    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, Spacious, bright and outward room studio with fireplace for a relaxing or romantic getaway. The fireplace area is a favorite spot for people, who enjoy quiet, relaxing and private time. The studio also comes with a modern, fully equipped bathroom, Laundry and plenty of closet space. LBGTQ...
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    Meriden, Connecticut 06450
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Washington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Street is a mint condition 4 bedroom home with a heated pool, wonderful flat private quiet yard with a swing set far back from the street. The home is in Washington, the most desirable historic rural town in Litchfield County with wonderful restaurants, land preserves, private schools,...
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    Washington, Connecticut 06793
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Milford
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spectacular direct waterfront home with the modern conveniences! Wake to the sounds of surf and breath taking sunrises. Relax and dine on the deck with grill. The home is naturally cooled by sea breezes or, there is also air conditioning, if you prefer. The beach house has 2 bedrooms, and 3 full...
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    Milford, Connecticut 06460
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Wits End Farm1 / 16
    (1)Excellent
    Bethlehem
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Our family stayed at Wits End Farm B&B for a weekend in early June for our son's graduation from a local boarding school. We can't say enough about our time there. Our host...
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    About this property
    This sophisticated and modernized 18th Century rambling farmhouse is set amount towering tress, huge lawns, flower beds, parterre vegetable and herb gardens, 2 ponds, stone walls, pasture and woods. There are five bedrooms, including one huge family suite with a Q bed, twin bed and a crib. All...
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    Bethlehem, Connecticut 06751
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Walk to private beach from this two bedroom home1 / 34
    (3)Excellent
    Branford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Good location, great restaurants near by, enjoyed sitting at Owenego club.Teresa was very friendly & more than accommodating!!!!Thanks for making it possible for us to...
    Reviewed 4 weeks ago
    The house is as described. It is very clean, very confortable, close to the Sound. There is a fish market a block from the house. This is a wonderful area for joggers or just...
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    About this property
    This is a two bedroom house with a king size bed in the master bedroom and a full size in the guest bedroom. The bathroom has a jacuzzi tub and large shower. There is wi-if, cable to, a patio and all amenities. This property sleeps 4 and is PET FRIENDLY. The rental comes with private access to the...
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    Location Information
    Branford, Connecticut 06405
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Branford
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Patio
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two acres of private New England charm over looking the Thimble Islands. Set atop a hill with a large rolling lawn perfect for all types of family lawn games.The vintage shingle stone home was built in 1932 for a wealthy Connecticut family. They created a sandy beach that rivals the size of the...
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    Location Information
    Branford, Connecticut 06405
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Branford
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Waterfront
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From generous picture windows enjoy views of Long Is. Sound and quaint Thimble Islands dotted with simple cottages and mansions. Large front room with a small kitchen hidden in a a 1930's armoire. A round dining table is lite from a 60" chandelier fit for a castle. Created by a professional...
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    Location Information
    Branford, Connecticut 06405
    Condo/Apartment - 1 Bathroom, Sleeps 3
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