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Holiday Rentals in Cheshire

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    Don't let other travellers get your favourite Cheshire area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 29 Rentals in Cheshire
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    The following rentals are within 30 kilometers of Cheshire.
    Middlefield
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Its the Perfect Weekend House just 80min from NYC!1 / 19
    (5)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    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
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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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    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/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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    Location Information
    New Haven, Connecticut 06512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stunning Waterfront Estate on Connecticut River1 / 38
    (1)Excellent
    Middle Haddam
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    This is a beautiful historic home on the CT River in Middle Haddam. I'm from CT but was not very familiar with the Haddam area and as it turns out this was one of the most...
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    About this property
    The Captain's House, a 3,400 SF 3-level renovated waterfront Victorian, features 5 bedrooms, 3-1/2 baths, gourmet kitchen,wraparound deck, badminton/volleyball court and 40' dock. A magical place to relax & recharge... Knowles Landing is one of the most beautiful waterfront estates on the...
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    Middle Haddam, Connecticut 06456
    Holiday Rental House - 5 Bedrooms, 3 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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    Beach House, Private Beaches, Casinos, Yale U1 / 19
    (10)Excellent
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    Great house. Charming. Well equipped with all the necessities. Very clean & quite. Beach is right there. Lanna is a doll. Very kind, accommodating, responsive to texts.
    Reviewed 4 November 2016
    This place was all that we wanted it to be. It was close to the beach (several doors), had a well equipped kitchen, comfy bed. Nice soft absorbent towels, a good shower, washer...
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    About this property
    Charming beach cottage, clean, well maintained interior,central AC. Cottage located on dead end street, 4 houses from LI Sound. Residents share PRIVATE BEACH.Guests of property also have beach rights to adjacent PRIVATE BEACH. View of ocean and salt marsh from front porch. Short walk to TOWN BEACH...
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    Location Information
    New Haven, Connecticut 06512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Guilford
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Porch
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located down a dirt road off of the beaten path. Enjoy an extraordinary country wooded vacation, holiday, getaway or reunion retreat for the two of you, the whole family, or up to 6-8 friends and family. Situated on 40 wooded acres of absolute privacy in the middle of 1100 acres of...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Newly remodeled 1891 Queen Anne Victorian mansion1 / 10
    (1)Excellent
    Wallingford
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Terrace
    • Air Conditioning
    • Patio
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Porch
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2017
    This was our first B&B and we had such an enjoyable stay. This Inn is beautifully decorated, clean and the inn keepers are so pleasant and attentive. Would certainly go back!
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    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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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled home with 4 bedrooms, 1.5 baths, family room, finished basement that can easily accommodate 8 people and is near everything. Just a quick commute to Yale, SCSU, Quinnipiac and University of New Haven, very close to the best restaurants in the greater New Haven area and within...
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    North Haven, Connecticut 06473
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    East Haven, Connecticut 06512
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Farmington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and unwind by the water when you stay at this 3-bedroom, 2-bathroom vacation rental house in Farmington. Situated in a quiet community, this home boasts accommodations for up to 6 guests and 2,200 square feet of living space. Spend your days exploring the area, visiting museums, or take a day...
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    Farmington, Connecticut 06032
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Middlefield
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/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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    Charming Waterfront Beach Cottage-WOW! Sunsets1 / 15
    (4)Excellent
    Guilford
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Porch
    • Waterfront
    • Shared Garden
    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2016
    The previous reviews are all pretty spot on. This is an incredibly charming, wonderful property that makes you feel like you're inhabiting a Wes Anderson movie. The location...
    Reviewed 19 September 2014
    If you are looking for an almost indescribably beautiful setting and a rustic, relaxing location, Seacliff is it. The view from the front screen porch and terrace is nothing...
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    About this property
    We love our cottage and you will too! 'Seacliff,' a classic turn of the century cedar shingled beach cottage, is located in the quiet Guilford, CT community of Mulberry Point. Direct water access for swimming, beachcombing, kayaking and fishing plus family-friendly association beach within a...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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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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    Wits End Farm B&B1 / 14
    (1)Excellent
    Bethlehem
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    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, 4 Bathrooms, Sleeps 10
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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)
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    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 / 17
    (5)Excellent
    Branford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    This home was just what we needed! The kitchen was well stocked with spices, some condiments and lots of dishes pots and pans. We were able to rent this home for less than a...
    Reviewed 8 September 2017
    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...
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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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    Branford, Connecticut 06405
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Meriden
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    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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    Guilford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Scenic and classic NE Shoreline Town of Guilford : The area boasts some of the best fishing, kayaking, sight seeing, hiking nearby nature trails and the third largest antique home collection in the State of CT. There is the 5 acre Guilford Green with boutique shopping, fabulous restaurants, food &...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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 15 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. If you find that you are traveling to Connecticut for work assignment or vacation, consider this option to hotel living. Our home will welcome you from travel or work with it's...
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    Cromwell, Connecticut 06457
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Meriden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 level Townhouse located in the Prestigious area of Mattabassett in Meriden. Enjoy beautiful Mountain View’s. Maintance free grounds, walking paths, ponds, pik nik tables, swings, baseball area, community pool (summertime) and so much more. Conveniently located to major highways,...
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    Meriden, Connecticut 06450
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • Cable/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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    Branford, Connecticut 06405
    Condo/Apartment - 1 Bathroom, Sleeps 3
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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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    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
    • Cable/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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    Location Information
    Hamden, Connecticut 06514
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Branford
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    • Patio
    • Cable/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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    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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