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Southbury Vacation Rentals

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    All 28 Rentals in Southbury
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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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    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    The following rentals are within 30 kilometres of Southbury.
    Milford
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Terrace
    • Balcony
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in beautiful Woodmont Beach and sits directly across the street from the water. Two fairly large rooms, one is a living room set up that has a large sofa great for lounging around, also has a twin memory foam mattress bed, kitchenette set up as shown in pic. Go through the...
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    Milford, Connecticut 06460
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Private 2 bedroom near Yale, downtown, great restaurants and parks1 / 9
    (1)Excellent
    Hamden
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Thank you to Geraldine for the opportunity to spend time in this good feeling, homey, rental space.We enjoyed the space, the gracious hospitality of our hosts, and the time they...
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    About this property
    Beautiful, clean, quiet, private 2 bedroom apartment on bus line. Minutes from Yale, downtown, parks, restaurants (best pizza in the world!!!) includes new stove, oven, large fridge. Plates, coffee machine, linens, tv, just bring fire stick or whatever you prefer to hook up to our free WiFi. No...
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    Hamden, Connecticut 06514
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Little House By the Sea1 / 22
    (1)Excellent
    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
    Reviewed August 3, 2018
    The location is amazing-a nice little community. At the end of the road is Lighthouse Point Park, which is right on the ocean. The house was immaculate-sooooo clean! Gloria has...
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    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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    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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    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    Reviewed July 21, 2014
    A spectacular week in a secluded spot and yet minutes from quaint New Milford Village. Pool is GREAT
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    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with...
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    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 24, 2017
    This review is long overdue. My mom and I stayed at this extraordinary home for close to a month and it couldn’t have been more perfect! The grounds were beautiful, a...
    Reviewed June 21, 2015
    We came to Woodbury to meet as a family & acknowledge the passing of our father in the town we all grew up in. Douglas was extremely helpful and encouraging in our arranging...
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    About this property
    My home has all the amenities for a perfect family/friends getaway. The chef's kitchen is fully equipped and totally at your disposal. Three good grocery stores and the 4.5 star New Morning Market and Health Food Store are nearby for your food shopping convenience. Most guests, however, prefer...
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    Location Information
    Woodbury, Connecticut 06798
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor a piece of Connecticut paradise at this 3-bedroom, 2-bathroom New Fairfield vacation rental house! Suitable for up to 10 guests, this Hampton-style home featuring an outdoor kitchen and 4 levels of outdoor space provides travelers with an ideal location on Candlewood Isle, where you can enjoy...
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    New Fairfield, Connecticut 06812
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • Internet Access
    • Balcony
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Master Bedroom with four additional bedrooms -- two are double height with lofts. The home features 18' soaring ceilings, an incredible wrap around deck overlooking lawns and gardens. Large Italian eat-in kitchen/family room. Office for 4. Home theater. Whole-house B&O system. Badminton, ping pong,...
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    Weston, Connecticut 06883
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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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 August 30, 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 August 30, 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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    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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    Jamaica Court Cottage1 / 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 June 21, 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 November 4, 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
    Beach House, Private Beaches, Casinos, Yale U 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...
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    New Haven, Connecticut 06512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Hamden, Connecticut 06514
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 2014
    We arrived all type A with many plans to hike and swim, ended up enjoying the comfort of the house, cooking, hanging out together. Switching from indoor seating for outdoor...
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    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $6,000 per month July $6,000 per month Aug $6,000 per month Memorial Day to Labor Day $14,000. During the winter months-mid-October-mid-March, I seek long term rentals. I only rent by the month during this...
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    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Easton
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our large and luxurious home is open to you for your enjoyment and relaxation. With 4 en-suite bedrooms and 2 additional bedrooms, the house is able to comfortably accommodate large groups of people for short stays. The house is in immaculate condition and boasts luxury appointments and and...
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    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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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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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Grill
    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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    Location Information
    North Haven, Connecticut 06473
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sherman
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private secure community with million dollar homes. Perfect weekend retreat. 90 minutes from NYC. This two bedroom cottage has all the necessary amenities. Includes access to two private beaches on Candlewood Lake and Green Pond. Just renovated with new wood floors, new appliances, new...
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    Sherman, Connecticut 06784
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Spacious 3 open bedrooms are available in a 2 floor open house close to Yale University. This beautiful open floor house features beautifully designed 2 open bedrooms(no walls/doors), open kitchen with gas stove, dishwasher, and a microwave. Has custom built-in furniture, lots of storage and...
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    New Haven, Connecticut 06511
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our apartment is very comfortable for either short-term or long-term stay. We have everything you may need. This fully furnished ground floor apartment features a spacious living room and separate bedroom with a comfortable queen size bed; Daybed with Trundle Set, Twin Size; two futons; additional...
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    Seymour, Connecticut 06483
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Weston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage sits on a family property in a small neighborhood (faces the main house on a circle driveway). It has been renovated with all new appliances and new floors while still maintaining it's cozy retreat feel. Each bedroom features a queen size bed. There is also a screened in porch for...
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    Weston, Connecticut 06883
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house has a soul. It is not like a fancy hotel but instead all elements of decor have some story to tell. The indoor is painted by an artist. We have grand piano which if you know how to play will make time together more fun. The pool is just amazing. Deep end has 8' and shallow 4.5'.We love it...
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    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Balcony
    • Washer
    • Parking
    • Terrace
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely house in North Haven, CT has been recently remodeled. It is centrally located and just minutes from Yale, Quinnipiac, UNH, SCSU and Albertus as well as shopping, the best restaurants, hiking trails in West Haven, Hamden and Wallingford, state parks and many local attractions including...
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    Location Information
    North Haven, Connecticut 06473
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    • Cable/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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    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Haven
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Located within walking distance of the North Haven Fair Grounds, our house is the perfect launch pad for your New England Adventure. We are just minutes from Yale, Quinnipiac, UNH, SCSU & Albertus, shopping, great restaurants, hiking trails, state parks and many local attractions including Stony...
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    Location Information
    North Haven, Connecticut 06473
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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