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Vacation Rentals in Stratford, CT and nearby

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All 44 Rentals in the Stratford Area
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The following rentals are within 20 miles of Stratford, Connecticut.

From
$250
Per Night
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1 / 7
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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From
$150
Per Night
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1 / 75
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Stratford, NY
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (7) Make Inquiry
From
$1,475
Per Week
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1 / 23
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Fairfield
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
From
$126
Per Night
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1 / 5
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Fairfield
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This 625 square foot fully furnished studio apartment sleeps 4-6 and consists of a bedroom area with queen sized bed (all linens supplied), living room (with hideabed and convertible futon), dining space, kitchen (with oven, microwave, refrigerator, toaster, dishwasher, coffee maker, dishes,... View all property information
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From
$250
Per Night
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1 / 24
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Rocky Point, NY
3 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Quaint 3 bedroom, 1 bath home, with beautiful views of the long island sound from the kitchen, dining area, bedroom, and back yard. Central air conditioning, cable, internet, phone. electric stove, fireplace, lovely enclosed front porch, large backyard, big gas barbeque grill. 3 minute walk to... View all property information
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5 of 5 stars Reviewed July 30, 2014
First off the house was very clean, very cozy and the view was amazing. When I showed up and my friends showed up we were all amazed of how nice the place was. Everything we...
5 of 5 stars Reviewed July 15, 2014
Our first time on eastern Long Island - the trip out from the hectic pace of NYC slowly turns from urban to beautiful parkland, finally ending at quaint Rocky Point LI. The home...
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From
$175
Per Night
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1 / 21
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North Fork... View all property information
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5 of 5 stars Reviewed October 14, 2014
Mark & Mona's historic apartment was a delight. It was small but cozy and clean. Our only surprise was that we didn't realize the bathroom was located inside one of the bedrooms...
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From
$295
Per Night
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1 / 17
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Southold, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Beautiful hardwood floors and... View all property information
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5 of 5 stars Reviewed August 28, 2014
We had such a wonderful time in Maureen and Alan's cottage. First and foremost, it's on Arshamomaque Pond, which looks like a lake but is actually an inlet of Peconic Bay. It's...
5 of 5 stars Reviewed July 13, 2014
My family was very pleased with these accommodations. We were all very comfortable. The place was very clean and well equipped for our 5 day stay. The location is absolutely...
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From
$175
Per Night
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1 / 21
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North... View all property information
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5 of 5 stars Reviewed June 3, 2014
I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
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From
$150
Per Night
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1 / 19
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Step back in time as you enter a Historic Home in the heart of Southold....the charm of the historic home is clear as you enter the front door of your unit into the inviting hallway and stairs to the entire upstairs of the home. Just part of the charm is the refinished original 1830 floors, lower... View all property information
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From
$300
Per Night
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1 / 15
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Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
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From
$250
Per Night
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1 / 18
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Representing the owner's suite is the Unit One apartment in the Historic White Blossom House. Newly renovated, floors, kitchen and bath completely updated. Kitchen updated with period country deep sink and fixtures. You will be very comfortable in this large apartment with living room, family... View all property information
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From
$250
Per Night
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1 / 13
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
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1 of 5 stars Reviewed September 2, 2012
The photos in the add looked good, particularly the garden and the proximity of the lake. We rented the place for four days. When we arrived, the first thing that struck us was...
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From
$695
Per Night
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1 / 42
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Weston
5 Bedrooms, 4 Bathrooms, Sleeps 8
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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,... View all property information
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From
$225
Per Night
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1 / 12
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the... View all property information
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From
$295
Per Night
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1 / 12
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Branford
Studio, 1 Bathroom, Sleeps 3
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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... View all property information
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From
$1,000
Per Night
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1 / 10
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Branford
5 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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... View all property information
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From
$130
Per Night
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1 / 15
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Branford
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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... View all property information
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5 of 5 stars Reviewed August 3, 2014
Last January we had set our eyes on the Ennis Cottage for the last two weeks of July and the long wait was worth it. For spending a holiday there is like uncorking your first...
5 of 5 stars Reviewed April 21, 2013
We had a very pleasant stay at the Ennis Cottage. The warm welcome we felt with Ron and his help getting around in and near Branford made us feel home and looking forward to...
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From
$300
Per Night
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1 / 14
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Fairfield
6 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Our family beach house is available for rent this July. Right on the sand, our beach house faces the Long Island Sound. The house has 6 bedrooms and an airy open plan lower floor, perfect for hosting guests or having family over. You'll love the spacious back patio with awning, the upper deck... View all property information
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From
$775
Per Night
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1 / 3
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Milford
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
4 bedroom, 3 full bathroom , Beach house, directly on the water View all property information
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From
$2,400
Per Week
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1 / 12
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Southold, NY
2 Bedrooms, Sleeps 6
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
**New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground,... View all property information
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From
$75
Per Night
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1 / 20
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Hamden
1 Bedroom, 1 Bathroom, Sleeps 3
Booking
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Amenities & Details
  • Grill
  • Internet Access
  • Mountain Views
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • x
About this property
Beautiful, modern, clean, SAFE, comfortable, and convenient to all transportation and highways. This stunner has a warm, inviting atmosphere with a hostess who is knowledgable about Connecticut AND New York City. The rental is a HIP, bright, basement apartment in a well appointed Colonial style... View all property information
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From
$257
Per Night
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1 / 17
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Sound Beach, NY
5 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located directly on the Long Island Sound, this home offers breathtaking panoramic water views. 5 bedrooms: 3 twins, 2 queens, and a king (in addition to a pull out queen sleeper sofa in the living room) 2 full bathrooms This home is ideal for unwinding and relaxing, the perfect place to find... View all property information
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From
$986
Per Night
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1 / 16
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Westport
4 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Elegant home was professionally designed to capture the spectacular views of the Ocean. The home was completely remodeled recently and includes a rich interior with state of the art kitchen appliances, wood burning fireplace, washer/dryer, central A/C and internet. Near the end of a quiet... View all property information
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From
$300
Per Night
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1 / 40
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Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Come experience a Northfork summer, golfing, biking, beaching, Estate sale hunting, in the Heart of Wine Country, Long Island. Centrally Located in the Town of Southold, South of the main road, 3 houses from the water in the elite Founders Landing section of North Fork, The cottage is minutes'... View all property information
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From
$235
Per Night
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1 / 6
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Stratford, NY
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Direct waterfront house with breathtaking views of Long Island Sound. Private beach. View all property information
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From
$91
Per Night
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1 / 23
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Port Jefferson Station, NY
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
A very spacious 1 bedroom private Apartment like, Bedroom can be configured to accommodate 2, 3, 4 or 6 comfortably, Private full bathroom, Open Area consists of living area, kitchenette, Mid size refrigerator, counter top with sink and cabinets, Toaster oven, microwave, Coffee machine etc.. ,... View all property information
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5 of 5 stars Reviewed December 24, 2014
We were born and raised on Long Island and go back every couple of years to visit. Most of the time we stay at a hotel or maybe an Inn / B&B. We came across this rental and it...
5 of 5 stars Reviewed October 8, 2014
Both owners were very personable and made us feel so comfortable. Attention to detail and making our visit feel like home was definitely accomplished beyond expectations.
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From
$149
Per Night
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1 / 27
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Southbury
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
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... View all property information
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From
$8,000
Per Month
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1 / 76
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Fairfield
5 Bedrooms, 5 Bathrooms, Sleeps 7
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
5 bedroom, 5 bath for rent in ultra exclusive Greenfield Hills area. Approx. 2 1/4 majestic acres, with a distant winter view of the Long Island Sound. A tranquil pond to the east, adjoining the Stillman Wildlife Preserve, Evergreens to the North, this estate is surrounded by multi million dollar... View all property information
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From
$350
Per Night
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1 / 2
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Rowayton
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Use of sailboat,paddelboard,kayak and small motor boat, swim and tennis in rowayton ct. 06853- walk to quaint village- furnished apt. For 2, with balcony on your own private swimming beach. Balcony overlooks the beach and the sound.-train 55 min. To grand central nyc. Unique vacation spot!... View all property information
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From
$171
Per Night
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1 / 19
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New Haven
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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... View all property information
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4 of 5 stars Reviewed December 5, 2014
This is a well equipped and furnished property. It was very clean and comfortable and WiFi and telephone were included. The house is only a few yards from the beach and, for...
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From
$250
Per Night
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1 / 11
Southold, NY
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
John Andrew's Cottage is a 'turnkey' experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a... View all property information
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4 of 5 stars Reviewed August 22, 2014
my daughter (5 1/2 year old) and i had a great visit here. the cottage was cute and comfortable. having the backyard was great too. the hosts were very friendly and...
5 of 5 stars Reviewed August 26, 2013
We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and...
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From
$195
Per Night
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1 / 8
Port Jefferson, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (13) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
A true retreat! Peace and serenity....these will be your thoughts as you look out and view the harbor and magnificient woods located on 3 acres! We are minutes away from a very lively town with many restaurants, theatre and shopping! We have beautiful restaurants on the water as well!! This... View all property information
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5 of 5 stars Reviewed October 16, 2014
Just as the review below I cannot say enough about this great vacation retreat. This is truly a wonderful vacation destination. Port Jefferson village is a great small village...
5 of 5 stars Reviewed September 22, 2014
This is a lovely rental with friendly hosts and walk-to-town convenience. We enjoyed the beautiful seclusion, lovely view (especially at night when the harbor lights are aglow...
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From
$225
Per Night
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1 / 22
Rocky Point, NY
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This breathtaking seaside cottage neighbors a 50 acre preserve with trails that lead to scenic views along the bluffs. This house was originally a boathouse that was pulled up from the beach and put onto a lot that was carved out of a huge sand dune. It has been completely renovated with an open... View all property information
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4 of 5 stars Reviewed July 13, 2014
The house was great, had almost everything, everything easy to use. Enjoyed the Jacuzzi, fire pit, and kayaks. Right in the middle of the island so nothing too far away. The house...
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From
$350
Per Night
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1 / 24
Port Jefferson, NY
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Hot Tub
  • Internet Access
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This five bedroom Harbor View home is only steps away from town and the dock, located in the village of Port Jefferson. It has the most amazing harbor views with stairs that lead straight to the harbor where you will find outstanding restaurants, night clubs, bars and shops! There is always... View all property information
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From
$500
Per Night
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1 / 20
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Southold, NY
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
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4 of 5 stars Reviewed June 16, 2014
We found the farmhouse to be charming and spacious for our seven family members. The location was beautiful with the vineyards and private beach, and it was also very handy for...
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From
$172
Per Night
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1 / 19
Payment Protection
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy, and... View all property information
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5 of 5 stars Reviewed August 18, 2013
This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
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From
$295
Per Night
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1 / 10
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Newly renovated waterfront cottage with detached studio This property consists of two separate buildings, a two bedroom house and a detached studio cottage . From September through June only the studio (sleeps 2) is available for rent. In July and August both the 2 bedroom cottage and the studio... View all property information
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From
$250
Per Night
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1 / 12
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award-winning wineries, antique shops, art galleries, and... View all property information
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From
$200
Per Night
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1 / 8
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the peaceful country... View all property information
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From
$321
Per Night
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1 / 5
Southold, NY
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central... View all property information
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From
$499
Per Night
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1 / 8
Southold, NY
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet in Southold, with... View all property information
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From
$295
Per Night
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1 / 11
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable... View all property information
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From
$167
Per Night
View Details
1 / 16
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and... View all property information
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1 / 6
Payment Protection
Fairfield
Studio, 2 Bathrooms, Sleeps 3
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden or Yard
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
2 bedroom / 2 bath FURNISHED rental for 5 months starting December.Fully equipped kitchen, linens, views of Long Island Sound,close to town center restaurants, etc.Modern,spacious,with fireplace, steam shower, jacuzzi tub,washer/dryer dishwasher etc. This is a luxury home away from home! No... View all property information
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Suitability

  • Wheelchair access (5)
  • Elder access (23)
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  • Pet friendly (15)
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