Cheshire, Connecticut Vacation Rentals

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Location: Cheshire, CT undo
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1 - 20 of about 448 from 8 sites
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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: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: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 with Queen, two twins with pullout beds and the detached studio cottage with queen bed . From ... 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:Oakdale, Connecticut
Bedrooms:1
Bathrooms:1
Sleeps:4
Property Type:Vacation Home

Amenities:Alarm Clock, BBQ, Beachfront View, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Full kitchen, Hair Dryer, Internet Access, Iron, Lakefront, Laundry, Linens, Microwave, Oceanfront, Oven, Pets OK, Phone, Refrigerator, Smoking OK, Stereo, Stove, TV, Toaster, Towels & more amenities »
Activities:Beach, Boating, Fishing, Kayaking, Swimming, Tubing & more activities »

Description: Small cozy cottage, direct lakefront with private sandy beach. Perfect for that getaway. The lake offers fishing, swimming,boating and kayaking. ... more details »
Location:Cutchogue, New York
Bedrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Basketball Court, Blender, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Full kitchen, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stove, TV, Toaster & more amenities »
Activities:Basketball, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Ice Skating, Jetskiing, Sailing, Shopping, Snorkeling, Tennis, Theme Parks, Water Parks, Water Skiing & more activities »

Description: This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms, one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the ... more details »
Location:Farmington, Connecticut
Bedrooms:6
Sleeps:12
Property Type:Vacation Home

Amenities:Air Conditioning, Balcony, Basketball Court, Deck, Fireplace, Full kitchen, Garage, Internet Access, Linens, Patio, Pets OK, Playground, Restaurant, Smoking OK, Swimming Pool, Towels & more amenities »
Activities:Amusement Parks, Basketball, Beach, Boating, Bowling, Canoeing, Casino, Fishing, Golf, Gym, Hiking, Horseback Riding, Ice Skating, Miniature Golf, Racquetball, Sailing, Shopping, Snow Skiing, Snowmobiling, Tennis, Theme Parks, Volleyball, Water Parks, Zoo & more activities »

Description: magnificant French Normandy hillside all brick 6 bedroom 7.5 bath custom Mansion with 3.5 acres beautiful, lush, private, exclusive ESTATE, in prestigious FARMINGTON, CT. Just at I-84, Exit 39. May be leased for long weekends, ... more details »
Location:Kent, Connecticut
Bedrooms:2
Sleeps:4
Property Type:Apartment

Amenities:Air Conditioning, Backyard, Basketball Court, Coffee Maker, Dishwasher, Full kitchen, Internet Access, Iron, Laundry, Linens, Microwave, Oven, Patio, Pets OK, Playground, Refrigerator, Restaurant, Smoking OK, Stove, Toaster, Wireless Internet Access & more amenities »
Activities:Basketball, Beach, Boating, Bowling, Fishing, Golf, Hiking, Horseback Riding, Hunting, Ice Skating, Kayaking, Restaurants, Sailing, Shopping, Snow Skiing, Tennis & more activities »

Description: Nestled in the heart of the village, this private get-away awaits you. Relax and still be in the center of everything. 2 bedrooms, 1 1/2 baths and charming backyard. There is wifi, fully equipped kitchen ... 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: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: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:Southfield, Massachusetts
Bedrooms:3
Sleeps:6
Property Type:Vacation Home

Amenities:BBQ, Breakfast Bar, Cable/Satellite TV, Coffee Maker, Computer Access, DVD Player, Dishwasher, Full kitchen, Garage, Hair Dryer, Iron, Laundry, Linens, Microwave, Mountain View, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, Woodburning Stove & more amenities »
Activities:Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Miniature Golf, Shopping, Snow Skiing & more activities »

Description: Peaceful home set on 3-acres with mountain views and a sunny Southern exposure. Kitchen is oversized with an eating area and a breakfast bar. Front porch and patio, master bedroom with ample storage and private ... 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: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: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:New Milford, Connecticut
Bedrooms:4
Bathrooms:2
Sleeps:8
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, CD Player, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Internet Access, Iron, Kitchenette, Laundry, Linens, Microwave, Outdoor Shower, Oven, Pets OK, Phone, Playground, Refrigerator, Restaurant, Screened Porch, Smoking OK, Stereo, Stove, Swimming Pool, TV, Toaster, VCR, Woodburning Stove & more amenities »
Activities:Beach, Boating, Bowling, Canoeing, Fishing, Golf, Gym, Hiking, Horseback Riding, Ice Skating, Jetskiing, Kayaking, Miniature Golf, Scuba Diving, Shopping, Snow Skiing, Snowmobiling, Tennis, Theme Parks, Water Parks, Water Skiing & more activities »

Description: SUMMER RENTAL LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful , very private country setting, four bedrooms, large family room with cathedral ceilings, grand piano. All amenities:cable TV, CD, DVD,VCR, internet. All rooms are with AC. ... more details »
Location:East Hampton, New York
Bedrooms:4
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Blender, Cable/Satellite TV, Coffee Maker, Deck, Dishwasher, Fireplace, Full kitchen, Garage, Hair Dryer, Hot Tub, Internet Access, Iron, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Phone, Playground, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster, Towels & more amenities »
Activities:Beach, Biking, Boating, Canoeing, Fishing, Golf, Gym, Hiking, Jetskiing, Kayaking, Ping Pong, Sailing, Scuba Diving, Shopping, Snorkeling, Snow Skiing, Surfing, Tennis, Water Skiing, Windsurfing & more activities »

Description: Built in 2004, this two story beautiful home is located on over two acres within the gorgeous white pines of the secluded Northwest Woods in East Hampton. It is located 1/2 mile from two beautiful ... more details »
Location:Otis, Massachusetts
Bedrooms:1
Bathrooms:1
Sleeps:4
Property Type:Apartment

Amenities:Child Friendly, Deck, Hot Tub, Laundry, Linens, Non-Smoking, Patio, Swimming Pool, Towels, Wireless Internet Access & more amenities »
Activities:Golf, Gym, Restaurants, Shopping, Swimming & more activities »

Description: Stay in this fabulous one bedroom with king bed and queen sized sleeper sofa right across from the clubhouse, workout room, hot tub, and pools at the private golf resort of Pointe Royale. Close to ... more details »
Location:Sag Harbor, New York
Bedrooms:4
Bathrooms:3
Sleeps:6
Property Type:Vacation Home

Amenities:Child Friendly
Activities:Beach

Description: Walk in to the view of the sky and bay through the living room. The master suite is its own floor. the house is modern, there are three other bedrooms. Perfect home for a summer ... more details »
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