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Brewster Holiday Homes

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    All 31 Rentals in Brewster
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    Don't let other travellers get your favourite Brewster area holiday rental. You're so close to securing your perfect getaway. Book today.
    The following rentals are within 30 kilometres of Brewster.
    Beacon
    3 Bedrooms, Sleeps 4Quick View
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    Cold Spring
    3 Reviews
    4 Bedrooms, Sleeps 7Quick View
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    New Milford, CT
    4 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    Beacon
    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Grill
    • Porch
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PLEASE NOTE: I DO NOT RENT FOR FOR 1 NIGHT. THERE IS A 2 NIGHT MINIMUM. Continue reading further down in this box for 5***** Reviews. Here's a sample: "More like a boutique hotel." "This house is a dream come true." "Great owner, great location!" This home in beautiful Hudson Valley is a...
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    Beacon, New York 12508
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cold Spring
    5 Reviews
    3 Bedrooms, Sleeps 5Quick View
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    • Grill
    • Washer
    • Mountain Views
    • Internet Access
    • DVD Player
    • Outdoor Dining Area
    • Parking
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 2 December 2013
    My parents visit me every year in New York City and this year we wanted to get out of the city. I did some research and came upon this place and took a leap of faith, renting it...
    Excellent of 5 bubbles
    Reviewed 12 August 2013
    The house very appealing and well equipped and the owner is very pleasant, informative and easy to work with. There is glass all around to view the spectacular wooded...
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    About this property
    This cozy 3 bedroom lakeside deck house is perfect for a small family (pet friendly!) to spend a weekend, a week or a whole month. Nestled in the woods near Cold Spring, NY on the Hudson River, an hour and 20 minutes from Manhattan, the property includes a small lake perfect for cool summer swims...
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    Cold Spring, New York 10516
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Mohegan Lake
    1 Bedroom, Sleeps 4Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a great getaway come visit the Hudson valley. Hikers welcome as historic Peekskill and Bear Mountain is only 10 minutes drive. A beautiful apartment with private entrance Kid friendly apartment with your own kitchen and private bathroom. Enjoy the quiet of the country side but know...
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    Mohegan Lake, Westchester County 10547
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pawling
    10 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Parking
    • Porch
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 1 March 2017
    We had booked this home for a group of girl friend attending a show at Daryl's House. We all loved the house it was charming and quaint but also very comfortable, spotlessly...
    Excellent of 5 bubbles
    Reviewed 20 February 2017
    Great house! Cute town within walking distance. The house is so comfortable you may not want to go out! If we go back to Pawling, I'd definitely stay here again. I highly...
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    About this property
    Historic beauty built in 1900 in the heart of the village Town of Pawling only a 90 min metro north train ride from Manhattan and no need for a car you can walk to the house and to most things or take a local taxi if needed for places outside of the village. .. Short walk to Metro North train(2...
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    Pawling, New York 12564
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beacon
    3 Bedrooms, Sleeps 7Quick View
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    • DVD Player
    • Patio
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All the comforts of home smack dab in the middle of all the best that Beacon has to offer. This airy 1920s bungalow is 3 blocks from cafe's, antique shops, and great restaurants on Main St. There is a fireplace, large eat-in kitchen, 6 person dining table, brand new bathroom, great backyard and...
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    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Wingdale
    4 Bedrooms, Sleeps 11Quick View
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    • DVD Player
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Mountain Views
    • Washer
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all in this vacation home on private lake and nature preserve nestled in the foothills of the Berkshires. Perched on a peninsula on the shores of Lake Weil (viewable via Google map), this stunning 4-bedroom contemporary home offers exclusive use of your own 30-acre lake. Pack a...
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    Wingdale, New York 12594
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    South Salem
    3 Bedrooms, Sleeps 8Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful 2500sqf, 3 bedroom 2.5 bathroom home located on 6 acres is decorated with modern and contemporary art creating a homey and comfortable environment which you will enjoy during your stay here. The privacy and quiet is paralleled only by the view of the woods which you can see from the...
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    Location Information
    South Salem, Westchester County 10606
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Chappaqua
    1 Bedroom, Sleeps 4Quick View
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    • Terrace
    • Parking
    • Balcony
    • Air Conditioning
    • Internet Access
    • Shared Garden
    • Outdoor Dining Area
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage at Stone Croft is a quick train ride to Manhattan, but looks out on woods and a stream. The cottage is like a two story suite with a full kitchen. There is a queen bed in the main bedroom and a queen sofa bed upstairs. A great place for families and kids. There is a dishwasher,...
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    Chappaqua, Westchester County 10514
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Stamford, CT
    2 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Balcony
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 21 August 2015
    The apartment was in a lovely setting, attached to the family house, but totally private. Liz the landlord was very friendly, helpful and knowledgeable of the area. The...
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    About this property
    Completely updated apartment in lovely rural setting but close to everything. Get away without going very far. Take a break from sterile hotel rooms while on business. Private entrance, 2 bedroom, 1.5 bath, fully equipped kitchen, dining room, living room, french doors to patio, balcony off...
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    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    New Milford, CT
    5 Bedrooms, Sleeps 10Quick View
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    • Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1840 completely renovated country house with lots of room, convenience and quietness. 4,000 sq. ft. furnished with many antiques. A most unique country kitchen, formal dining room, eat-in kitchen, library, living room, den, five bedrooms (some have "Sleep Number" mattresses), and 5 and a half...
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    New Milford, Connecticut 06776
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Beacon
    1 Bedroom, Sleeps 4Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming and cozy mini apartment with a private entrance, west end of Beacon. Steps from historic Main Street, shopping and Metro North train station. My place is good for couples, solo adventurers, and business travelers. Quiet residential neighborhood just off Main Street close to galleries,...
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    Location Information
    Beacon, New York 12508
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Croton on Hudson
    8 Bedrooms, Sleeps 24Quick View
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    • Balcony
    • Housekeeping Included
    • Patio
    • DVD Player
    • Washer
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded and Private estate on over 100 protected acres.this historically significant 1895 estate boasts a lot of extras. Tennis court, hiking trails, fishing, golf course 4 miles away, meticulously maintained, each room tastefully decorated, immaculate. Cook's gourmet kitchen includes Viking...
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    Croton on Hudson, Westchester County 10520
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Weston, CT
    5 Bedrooms, Sleeps 8Quick View
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    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • Internet Access
    • Balcony
    • Washer
    • 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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    Ridgefield, CT
    8 Bedrooms, Sleeps 12Quick View
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    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The legendary Sunset Hall has captivated the hearts of its keepers since built for ambassador James Stokes in 1912 at Ridgefield's highest point to afford 50 mile views of the NY skyline and panoramic vistas of Round Pond from the widow walk perch. This regal Georgian has delighted subsequent...
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    Location Information
    Ridgefield, Connecticut 06877
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 12
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    Garrison
    3 Bedrooms, Sleeps 6Quick View
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    • Patio
    • Satellite TV
    • Private Garden
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 1400 sq. ft. Saltbox style home was built in the early 1980's. It sits on 2.25 acres. with each room having a view of the garden that surrounds the house. Our road is a neighborhood of friends, young and old. In an hour we can be at the top of a mountain looking down on the Hudson River and...
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    Garrison, New York 10524
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Base Camp - Dutch Colonial Estate
    Beacon
    1 Bedroom, Sleeps 2Quick View
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private getaway at the base of Mt. Beacon. Easy access to hiking trails and walking distance to downtown Beacon. Views of the Hudson Valley from the front exposure, and mountains to the rear. Large airy bedroom with a beautiful tiled bath. The Space The maid's wing of our brick Dutch colonial...
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    Beacon, New York 12508
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Fort Montgomery
    1 Bedroom, Sleeps 4Quick View
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    • Air Conditioning
    • Secure Parking
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Fort Montgomery, New York 10922
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Weston, CT
    2 Bedrooms, Sleeps 4Quick View
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    • Satellite TV
    • Wi-Fi
    • Parking
    Suitability
    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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    Location Information
    Weston, Connecticut 06883
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Salem
    1 Bedroom, Sleeps 5Quick View
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    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gracious and well appointed Coach House has been beautifully renovated. The Light and Airy Two Floor cottage is situated on the property of an historic home, and offers a Pool, mature gardens, riding and hiking trails. It's near excellent fishing spots. Dine al fresco on your private patio!...
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    Location Information
    North Salem, Westchester County 10560
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Newtown, CT
    3 Bedrooms, Sleeps 6Quick View
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    • Washer
    • Housekeeping Included
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A historic and charming three bedroom, two bath saltbox farmhouse on the grounds of the beautiful and private McLaughlin Vineyards. The house is conveniently located in Northern Fairfield County, about four miles from I-84 and only 90 minutes from mid-town Manhattan. With a large expansive front...
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    Location Information
    Newtown, Connecticut 06482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Croton on Hudson
    1 Bedroom, Sleeps 2Quick View
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    • Air Conditioning
    • Mountain Views
    • Grill
    • Balcony
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The apartment is attached to the main house with a separate,private entrance. The apartment exits onto a patio next to the pool. It has a living room, bathroom and kitchen. Fully furnished. It is located on 3 acres of lawn and woodland. It is quiet. We are 48 minutes by train from mid...
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    Croton on Hudson, Westchester County 10520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cortlandt Manor
    1 Bedroom, Sleeps 2Quick View
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    • Porch
    • Grill
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an independent room with separate access. The room is fully furnished with a queen bed, breakfast table, couch, Cable TV and internet. The room also has a separate kitchen and a shared laundry. The guests are allowed to cook with an electric /induction stove.Two miles from Annesville creek...
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    Cortlandt Manor, Cortlandt 10567
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Pound Ridge
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A luxury cottage set privately on a 7 acre estate in sylvan Pound Ridge, New York. A perfect setting from which to explore Westchester's horse country, The Hudson Valley, New England's Connecticut villages and New York City. World renowned restaurants are within minutes and recreational activities...
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    Pound Ridge, Westchester County 10576
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Easton, CT
    6 Bedrooms, Sleeps 20Quick 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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    Roxbury, CT
    2 Bedrooms, Sleeps 4Quick 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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    Stamford, CT
    1 Bedroom, Sleeps 2Quick View
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    • Central Heating
    • Housekeeping Included
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In this high-ceiling sunny downtown loft, there is a family atmosphere and eclectic furniture and decor. It is close to local activities (parades, fun-raisers, fun runs...etc), great nightlife, public transport: the bus is across the street, the city center (only a 1/4 mile away), restaurants,...
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    Stamford, Connecticut 06905
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Easton, CT
    6 Bedrooms, Sleeps 12Quick View
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    • Air Conditioning
    • Shared Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Jan 02 : Tuesday, Thursday, Wednesday, Friday, Monday, Saturday and Sunday check-in required, Tuesday, Thursday, Wednesday, Friday, Monday, Saturday and Sunday check-out required.; Our large and luxurious home is open to you...
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    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Stormville
    4 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Sauna
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Far View Farm is located on Stormville Mountain. This offers breath taking views of the Hudson Valley. This farmhouse goes back to the early 1800's but has everything to make it a private retreat from your busy life. It has 25 private acres with trails and no neighbors to be seen. Enjoy the views...
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    Location Information
    Stormville, New York 12582
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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