Cheshire, Connecticut Vacation Rentals

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Location: Cheshire, CT undo
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1 - 20 of about 506 from 9 sites
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Location:Shelter Island Heights, New York
Bedrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, Covered Porch, Deck, Dishwasher, Fireplace, Full kitchen, Internet Access, Iron, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Basketball, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Ice Skating, Jetskiing, Kayaking, Miniature Golf, Parasailing, Racquetball, Sailing, Scuba Diving, Shopping, Snorkeling, Snowmobiling, Surfing, Tennis, Water Skiing, Whale watching, Windsurfing & more activities »

Description: With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. ... more details »
Location:Putnam Valley, New York
Bedrooms:3
Bathrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Balcony, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Lake View, Lakefront, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, Stove, TV, Toaster, VCR & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Hiking, Jetskiing, Kayaking, Sailing, Scuba Diving, Shopping, Snorkeling, Tennis, Water Skiing, Windsurfing & more activities »

Description: Lake Oscawana surrounds three sides of the Rock on which the House stands. The lake is a 2.5 mile long stream- and spring-fed freshwater lake hidden in the Hudson Highlands. The unique siting gives privacy, ... more details »
Location:Westhampton, New York
Bedrooms:4
Bathrooms:4
Sleeps:12
Property Type:Apartment

Amenities:Air Conditioning, Blender, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Full kitchen, Iron, Laundry, Microwave, Oven, Pets OK, Refrigerator, Restaurant, Smoking OK, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Beach, Shopping

Description: Private contemporary vacation home available for rent during the spring/summer/fall season in beautiful Westhampton Beach. Four (4) Bedroom/ Four (4) Bath 2-story home including 20 x 40 in-ground pool amongst expansive deck area with plenty ... more details »
Location:Stormville, New York
Bedrooms:4
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Hot Tub, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Refrigerator, Sauna, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Basketball, Boating, Fishing, Hunting, Kayaking, Miniature Golf, Snow Skiing, Snowmobiling, Tennis, Water Parks & more activities »

Description: 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 ... more details »
Location:Southampton, New York
Bedrooms:3
Bathrooms:2
Sleeps:7
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels, VCR & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Hiking, Horseback Riding, Miniature Golf, Shopping, Surfing, Water Parks, Water Skiing, Whale watching, Windsurfing, Zoo & more activities »

Description: Great escape in Southampton Village. Fully Furnished, Rate for Memorial Day to Labor Day is $30,000.00. June is $6500. July or August monthly is $15000. Easy to get to, Walk from the Train/Jitney 3 short ... more details »
Location:Orient Point, New York
Bedrooms:2
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Basketball Court, Beachfront View, Blender, Cable/Satellite TV, Coffee Maker, Dishwasher, Full kitchen, Internet Access, Laundry, Linens, Microwave, Oceanfront, Outdoor Shower, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stove, Swimming Pool, TV, Toaster, Wireless Internet Access & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Casino, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Jetskiing, Kayaking, Miniature Golf, Sailing, Scuba Diving, Shopping, Snorkeling, Tennis, Water Parks, Water Skiing, Windsurfing & more activities »

Description: All newly renovated and exquisitely appointed home sits on a half acre in the private community of Green Acres steps away from the beaches in unspoiled Orient Point. Designer Rena Wilhelm decorated the home in ... more details »
Location:Southampton, New York
Bedrooms:4
Sleeps:9
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Basketball Court, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Disability Access, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels, VCR & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Jetskiing, Kayaking, Miniature Golf, Parasailing, Racquetball, Sailing, Scuba Diving, Shopping, Snow Skiing, Surfing, Tennis, Water Parks, Water Skiing, Whale watching, Windsurfing, Zoo & more activities »

Description: Why rent 12 Bob White Drive in Water Mill summer of 2015? Secluded location only 15 minutes from villages of Sag Harbor, Bridgehampton, closeness to Southampton beaches without the traffic [15 minutes] Architect designed house ... more details »
Location:Southold, New York
Bedrooms:3
Bathrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Basketball Court, Beachfront View, Blender, Cable/Satellite TV, Coffee Maker, Deck, Disability Access, Dishwasher, Fireplace, Full kitchen, Internet Access, Iron, Kitchenette, Laundry, Linens, Microwave, Oceanfront, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stove, TV, Toaster & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Jetskiing, Kayaking, Miniature Golf, Parasailing, Sailing, Scuba Diving, Shopping, Snorkeling, Tennis, Water Parks, Water Skiing, Windsurfing & more activities »

Description: 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 ... more details »
Location:Hampton Bays, New York
Bedrooms:2
Bathrooms:1
Sleeps:4
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, CD Player, Cable/Satellite TV, Coffee Maker, Computer Access, DVD Player, Deck, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stove, TV, Toaster, Towels, VCR, Woodburning Stove & more amenities »
Activities:Basketball, Beach, Biking, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Jetskiing, Miniature Golf, Sailing, Scuba Diving, Shopping, Snorkeling, Surfing, Tennis, Water Skiing & more activities »

Description: Ideal get-a-way home, minutes from bay and beach, on 1/3 acre wooded lot. This home away from home is fully equipped with all the desired amanities. Central air condition. Fully equipped kitchen: gas oven and ... more details »
Location:East Hampton, New York
Bedrooms:3
Bathrooms:3
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Hot Tub, Internet Access, Iron, Laundry, Linens, Microwave, Outdoor Shower, Oven, Pets OK, Phone, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels, VCR & more amenities »
Activities:Basketball, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Ice Skating, Kayaking, Miniature Golf, Parasailing, Racquetball, Sailing, Scuba Diving, Shopping, Snorkeling, Snowmobiling, Surfing, Theme Parks, Volleyball, Water Parks, Water Skiing, Whale watching, Windsurfing & more activities »

Description: This immaculate Ralph Lauren furnished home has it all including a Hot Springs Spa, custom Heated Pool with stand alone Pool House, 3000 sq. ft. of decking that wraps around entire back of home leading ... more details »
Location:Southold, New York
Bedrooms:3
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, Deck, Disability Access, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Shower, Smoking OK, Stove, TV, Toaster & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Jetskiing, Kayaking, Miniature Golf, Sailing, Scuba Diving, Shopping, Snorkeling, Tennis, Water Parks, Water Skiing, Windsurfing & more activities »

Description: 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 ... more details »
Location:Southold, New York
Bedrooms:2
Bathrooms:1
Sleeps:4
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Backyard, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Laundry, Microwave, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stove, Sunroom, TV, Toaster & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Hunting, Kayaking, Miniature Golf, Sailing, Scuba Diving, Shopping, Snorkeling, Surfing, Tennis, Theme Parks, Water Parks, Water Skiing, Windsurfing & more activities »

Description: 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 ... more details »
Location:Sound Beach, New York
Bedrooms:3
Bathrooms:2
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, CD Player, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Laundry, Linens, Microwave, Oceanfront, Outdoor Shower, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, TV, Toaster, Towels, VCR & more amenities »
Activities:Basketball, Beach, Boating, Fishing, Golf, Hiking, Kayaking, Ping Pong, Sailing, Shopping, Surfing, Tennis, Water Parks, Windsurfing & more activities »

Description: WATERFRONT BEACH HOUSE - SOUND BEACH - Long Island Located on the bluff with amazing views of the Long Island Sound around the year. 1:15 min drive (60 miles) from Manhattan. 25 min. from the ... more details »
Location:Shelter Island, New York
Bedrooms:3
Bathrooms:3
Sleeps:5
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Laundry, Linens, Outdoor Shower, Oven, Pets OK, Phone, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, Towels & more amenities »
Activities:Beach, Biking, Boating, Fishing, Hiking, Horseback Riding, Kayaking, Miniature Golf, Sailing, Shopping, Tennis & more activities »

Description: Contemporary, light filled 3 bedroom, 3 bath home located near South Ferry with easy access to the Hamptons. The lovely open floor plan features an array of contemporary art and sculptures, a living room with ... more details »
Location:Hampton Bays, New York
Bedrooms:1
Bathrooms:1
Sleeps:2
Property Type:Apartment

Amenities:Air Conditioning, Alarm Clock, BBQ, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, Deck, Hair Dryer, Internet Access, Iron, Linens, Microwave, Pets OK, Refrigerator, Restaurant, Smoking OK, TV, Toaster, Towels & more amenities »
Activities:Basketball, Beach, Hiking

Description: Attached to owner-occupied home, yet very private and secluded. Fully furnished (art and antiques) and equipped, from wine opener to beach chairs. Adjacent to park and Paumanok Trail for hiking. Other trails nearby.. Perfect for ... more details »
Location:Sag Harbor, New York
Bedrooms:3
Sleeps:13
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Basketball Court, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Disability Access, Dishwasher, Fireplace, Full kitchen, Internet Access, Iron, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Sauna, Smoking OK, Stereo, Swimming Pool, TV, Toaster, Towels & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Miniature Golf, Parasailing, Racquetball, Sailing, Scuba Diving, Shopping, Snorkeling, Surfing, Tennis, Volleyball, Water Skiing, Windsurfing & more activities »

Description: Excellent central location in the heart of it all. Two minutes to the village from this handsome two-story light and bright contemporary home situated on a beautifully landscaped half acre property with a free-form heated ... more details »
Location:Cutchogue, New York
Bedrooms:3
Bathrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels, VCR & more amenities »
Activities:Beach, Biking, Boating, Canoeing, Fishing, Golf, Hiking, Horseback Riding, Restaurants, Sailing, Tennis, Water Skiing, Windsurfing & more activities »

Description: Looking for a great summer retreat? Restaurants, antiquing, wineries, biking, canoeing, tennis, golf and of course the beach are all yours to be had at this charming east end gem on laid back Shelter Island. ... more details »
Location:Copake, New York
Bedrooms:3
Bathrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, DVD Player, Deck, Dishwasher, Full kitchen, Lake View, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Refrigerator, Restaurant, Smoking OK, TV, Toaster, Towels, VCR & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Hiking, Jetskiing, Kayaking, Sailing, Snow Skiing, Water Skiing & more activities »

Description: Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher ... more details »
Location:Westport, Connecticut
Bedrooms:3
Bathrooms:2
Sleeps:5
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Basketball Court, Beachfront View, Blender, CD Player, Computer Access, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Oceanfront, Pets OK, Restaurant, Smoking OK & more amenities »
Activities:Basketball, Beach, Biking, Boating, Canoeing, Fishing, Golf, Gym, Hiking, Jetskiing, Kayaking, Miniature Golf & more activities »

Description: We are looking for a summer rental for this exquisite home located directly on the beach in the charming town of Westport, CT. This beachfront home is on a private island located minutes from Compo ... more details »
Location:East Hampton, New York
Bedrooms:4
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Balcony, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Refrigerator, Restaurant, Smoking OK, Stove, Swimming Pool, TV, Toaster & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Kayaking, Sailing, Tennis, Water Skiing, Windsurfing & more activities »

Description: Sited perfectly on the eastern shore of beautiful Three Mile Harbor in East Hampton, Island View offers sweeping views of the water and a picturesque island in the foreground. Its ideal vantage point offers spectacular ... more details »
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