Cheshire, Connecticut Vacation Rentals

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Location: Cheshire, CT undo
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1 - 20 of about 645 from 10 sites
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Location:Center Moriches, New York
Bedrooms:5
Sleeps:10
Property Type:Vacation Home

Amenities:Deck, Jacuzzi, Linens, Patio & more amenities »
Activities:Beach, Boating, Fishing, Golf, Shopping, Water Parks & more activities »

Description: The space is the entire second floor of this oversized home overlooking Webby 's Beach, and the great Moriches Bay! Four very spacious bedrooms plus huge den (5th BR), Huge Chef 's Kitchen, Big Marble ... 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:Hampton Bays, New York
Bedrooms:7
Sleeps:18
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, DVD Player, Deck, Disability Access, Dishwasher, Fireplace, Full kitchen, Hair Dryer, Hot Tub, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Phone, Pool Table, Refrigerator, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels & more amenities »
Activities:Beach, Ping Pong, Restaurants

Description: Huge 7 bedroom contemporary with 4 1/2 baths, huge deck, in-ground pool, outdoor bar, 7 person hot tub, gas BBQ. Spectacular recreation room, wonderful for entertaining. Fully loaded kitchen, 10 minute drive to ocean beach, ... 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:East Marion, New York
Bedrooms:6
Bathrooms:5
Sleeps:12
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Kitchenette, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Phone, Refrigerator, Screened Porch, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels & more amenities »
Activities:Beach, Biking

Description: Escape to a private pastoral compound comprised of a historical home and a guest carriage house sitting on eight lush acres. The main country manor house offers three spacious bedrooms, including an en suite master ... more details »
Location:Bridgehampton, 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, Outdoor Shower, Oven, Patio, Pets OK, Phone, Refrigerator, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels, VCR & more amenities »
Activities:Beach, Gym, Hiking, Horseback Riding, Miniature Golf, Running, Sailing, Tennis, Water Skiing, Windsurfing & more activities »

Description: Centrally-located, south of the highway charmer with easy layout and all year round cozy feel. Sun drenched, post modern with vaulted ceilings, oversize windows and exposed beams running throughout house. Expansive great room is fantastic ... more details »
Location:Southold, New York
Bedrooms:3
Bathrooms:2
Sleeps:4
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Basketball Court, CD Player, Cable/Satellite TV, Ceiling fans, Coffee Maker, DVD Player, Deck, Fireplace, Full kitchen, Hot Tub, Internet Access, Jacuzzi, Laundry, Linens, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, Towels, Wireless Internet Access & more amenities »
Activities:Basketball, Beach, Biking, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Jetskiing, Kayaking, Miniature Golf, Sailing, Shopping, Tennis, Water Parks & more activities »

Description: 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, ... 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:Bridgehampton, New York
Bedrooms:1
Bathrooms:1
Sleeps:2
Property Type:Vacation Home

Amenities:Air Conditioning, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Refrigerator, Restaurant, Smoking OK, Stove, TV, Towels, VCR & more amenities »
Activities:Beach, Bowling, Fishing, Golf, Gym, Horseback Riding, Restaurants, Shopping, Surfing, Tennis & more activities »

Description: Bridgehampton Home, ideally located, near town, shopping and beaches. South Fork Attractions, Wine Tastings, great Restaurants, Farm Stands, Bay St theater and movies, all a short drive away. Your own room & bath in this ... more details »
Location:East Hampton, 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, Computer Access, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, Towels, VCR & more amenities »
Activities:Beach, Biking, Boating, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Kayaking, Miniature Golf, Sailing, Shopping, Snorkeling, Surfing, Tennis, Volleyball, Water Parks, Whale watching & more activities »

Description: This cottage is located on one of the nicest blocks in Springs area of East Hampton. The house is a cozy ranch, with a Cathedral ceiling in the living/dining area. Relax on our lovely deck ... more details »
Location:East Quogue, New York
Bedrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Fireplace, Hair Dryer, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stove, TV, Toaster, Towels & more amenities »
Activities:Amusement Parks, Beach, Biking, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Jetskiing, Kayaking, Miniature Golf, Sailing, Shopping, Surfing, Water Parks, Water Skiing, Whale watching, Windsurfing & more activities »

Description: This charming ranch home is conveniently located south of the highway in the idyllic village of East Quogue. Located on a quiet street this cedar shingled ranch home offers two bedrooms, one and a half ... 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 »
Location:West Cornwall, Connecticut
Bedrooms:4
Bathrooms:3
Sleeps:8
Property Type:Vacation Home

Amenities:BBQ, Cable/Satellite TV, DVD Player, Deck, Dishwasher, Full kitchen, Laundry, Linens, Microwave, Pets OK, Refrigerator, Restaurant, Smoking OK, Stereo, TV & more amenities »
Activities:Fishing, Kayaking, Shopping, Tennis & more activities »

Description: Antique Cornwall renovated farmhouse with wide floor boards on a quiet country road. One bedroom on main floor, new master bedroom suite upstairs. Eat in kitchen plus separate dining room. Large living room comfortably furnished. ... more details »
Location:Stanfordville, New York
Bathrooms:1
Sleeps:2
Property Type:Vacation Home

Amenities:Alarm Clock, BBQ, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Fireplace, Full kitchen, Hair Dryer, Internet Access, Lakefront, Linens, Microwave, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, Towels, VCR & more amenities »
Activities:Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Ice Skating, Shopping & more activities »

Description: ROMANTIC log cabin with lovely stone fireplace designed for only 2 sits on the shore of its own 3.5 acre lake on 85 acres of land. Your closest neighbor will be 1/4 mile away! Enjoy ... 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:8
Bathrooms:6
Sleeps:20
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Beachfront View, Blender, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Disability Access, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Hot Tub, Internet Access, Iron, Kitchenette, Laundry, Linens, Microwave, Oceanfront, Oven, Pets OK, Phone, Pool Table, Refrigerator, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, Towels & more amenities »
Activities:Beach, Fishing, Ping Pong

Description: Inspired by Walden, Thoreau and Emerson, Shell House is the quintessential luxury rental in the Hamptons. Dock in the nearby marina or rent a boat for the day. Shell House is your gateway to world ... more details »
Location:Port Jefferson, New York
Bedrooms:9
Bathrooms:2
Sleeps:2
Property Type:Vacation Home

Amenities:Alarm Clock, Basketball Court, Blender, CD Player, Cable/Satellite TV, DVD Player, Disability Access, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Laundry, Microwave, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, VCR & more amenities »
Activities:Amusement Parks, Basketball, Beach, Fishing, Golf, Gym, Hiking, Kayaking, Tennis, Volleyball & more activities »

Description: Large Home Set On Hilltop In Pt.Jeff Vill, 3 Bdrms, 2Full Baths, Beautiful Great Room, Oversized Windows,Crown Molding,10' Ceilings Throughout 1st Floor,,Port Jeff Ammen. ... more details »
Location:Wading River, New York
Bedrooms:4
Bathrooms:1
Sleeps:10
Property Type:Vacation Home

Amenities:CD Player, Cable/Satellite TV, Deck, Full kitchen, Hair Dryer, Iron, Laundry, Outdoor Shower, Oven, Pets OK, Restaurant, Stove, Towels, Wireless Internet Access & more amenities »
Activities:Beach, Jetskiing, Kayaking, Swimming & more activities »

Description: This beach house has panoramic views and a large wrap around deck, with a screened in porch. Full kitchen, full bath, outdoor shower. Your true beach house! Directly in the sand. nThis home is a ... more details »
Location:Stanfordville, New York
Bathrooms:1
Sleeps:2
Property Type:Vacation Home

Amenities:BBQ, Fireplace, Full kitchen
Activities:Hiking

Description: ROMANTIC log cabin with lovely stone fireplace designed for only 2 sits on the shore of its own 3.5 acre lake on 85 acres of land. Your closest neighbor will be 1/4 mile away! r ... more details »
Location:West Cornwall, Connecticut
Bedrooms:3
Bathrooms:3
Sleeps:10
Property Type:Vacation Home

Amenities:Air Conditioning, Child Friendly, Garage, Pets OK, Wireless Internet Access & more amenities »
Activities:Beach, Snow Skiing, Tennis

Description: Architect-designed, contemporary, 3-bedroom country home. Sited on five private hillside acres with breathtaking views of the Housatonic River Valley in the foothills of the Berkshire Mountains. With geothermal heating and air conditioning, heated floors, wood, ... more details »
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