Cheshire, Connecticut Vacation Rentals

optional
optional
optional
your search
Location: Cheshire, CT undo
refine your search
Location
Property Type
Region
Nightly Rate (median: 285)
Bedrooms
Bathrooms
Sleeps
Star-rating
Activities
Amenities

1 - 20 of about 395 from 7 sites
sort by: best match | distance nightly rate
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: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: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. Off- season (not summer) rates are $1500 per week or ... 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: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: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 setting with a home on 3-acres. Features 270 degree mountain views, a sunny southern exposure, and a front porch and patio to take in all the scenery. Kitchen is over sized with an eating ... 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: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: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:Mattituck, New York
Bedrooms:2
Bathrooms:1
Sleeps:5
Property Type:Vacation Home

Amenities:Air Conditioning, Alarm Clock, BBQ, Backyard, Cable/Satellite TV, Ceiling fans, Coffee Maker, DVD Player, Deck, Full kitchen, Garage, Internet Access, Iron, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Phone, Refrigerator, Restaurant, Screened Porch, Shower, Smoking OK, Stove, TV, Toaster, VCR & more amenities »
Activities:Beach, Biking, Fishing, Miniature Golf, Shopping & more activities »

Description: Lovely home on quiet private road . Three minute walk to the private beach .Front porch faces the sound. Can sleep up to five. Backyard hot/cold shower to rinse of after returning from the beach. ... more details »
Location:East Hampton, New York
Bedrooms:3
Sleeps:6
Property Type:Vacation Home

Amenities:Air Conditioning, BBQ, Cable/Satellite TV, Coffee Maker, DVD Player, Deck, Dishwasher, Fireplace, Full kitchen, Internet Access, Laundry, Linens, Microwave, Outdoor Shower, Oven, Patio, Pets OK, Refrigerator, Restaurant, Smoking OK, Stereo, Stove, TV, Toaster & more amenities »
Activities:Beach, Boating, Canoeing, Fishing, Golf, Gym, Hiking, Jetskiing, Kayaking, Sailing, Shopping, Surfing, Tennis & more activities »

Description: Enter through a quiet and tranquil sun room with slate flooring where glass French Doors will lead you into the main living area with hardwood floors, soaring cathedral ceilings and a great fireplace. The kitchen ... 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: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:Baiting Hollow, New York
Bedrooms:2
Bathrooms:2
Sleeps:6
Property Type:Vacation Home

Amenities:Child Friendly, Shower
Activities:Beach, Camping, Golf, Water Parks & more activities »

Description: Charming cottage in the woods just steps from the peaceful Long Island Sound. This cottage has two bedrooms and sleeps 6. Built in 1950, this cottage has been passed though two generations. Owned by one ... more details »
Location:Stamford, Connecticut
Bedrooms:2
Bathrooms:2
Sleeps:4
Property Type:Apartment

Amenities:BBQ, Backyard, Balcony, Full kitchen, Laundry, Patio, Refrigerator, TV, Wireless Internet Access & more amenities »
Activities:Restaurants, Shopping

Description: 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. n nPrivate entrance, 2 bedroom, 1.5 bath, fully ... more details »
Location:Meriden, Connecticut
Bedrooms:3
Bathrooms:5
Sleeps:4
Property Type:Apartment

Amenities:BBQ, Balcony, Elevator, Iron, Ironing Board, Pets OK, Sauna, Swimming Pool & more amenities »
Activities:Gym, Restaurants, Running

Description: Spacious and bright apartment in a prime location in Alphaville. nThis 3 bedroom apartment comes fully furnished with a touch of color that reflects it's owner's character! nYou will love relaxing on the sunny balcony ... more details »
Location:Southbridge, Massachusetts
Bedrooms:2
Bathrooms:1
Sleeps:4
Property Type:Apartment

Amenities:Air Conditioning, Child Friendly, DVD Player, Full kitchen, TV, Towels & more amenities »
Activities:Board Games, Restaurants, Shopping

Description: Located on an old and quite street,Roger Street is situated in front of a very nice brook. Of the right day you can see great blue heron fly a few feet above the water. n ... more details »
Location:East Hampton, New York
Bedrooms:4
Bathrooms:3
Sleeps:8
Property Type:Vacation Home

Amenities:BBQ, Child Friendly, Deck, Fire Pit, Fireplace, Pool Table, Shower, Swimming Pool, TV & more amenities »
Activities:Beach, Restaurants

Description: Post modern traditional farm house set on over an acre on quite Picturesque cul-de-sac walking distance to great bay beaches, boat launches, Parks, Marinas and restaurants. Five minute ride to village and ocean beaches. House ... more details »
Location:Bridgehampton, New York
Bedrooms:4
Bathrooms:5
Sleeps:9
Property Type:Vacation Home

Amenities:Air Conditioning, Child Friendly, Computer Access, DVD Player, Deck, Fireplace, Linens, Pets OK, Swimming Pool, TV, Towels, Wireless Internet Access & more amenities »

Description: Great house set on 2 acres and surrounded by 40 acres of reserve on 3 sides for complete privacy. Two masters with kings, two additional bedrooms and a den offer room for additional guests. The ... more details »
Location:Southampton, New York
Bedrooms:4
Bathrooms:4
Sleeps:9
Property Type:Vacation Home

Amenities:Air Conditioning, Blender, Coffee Maker, Crib, DVD Player, Disability Access, Internet Access, Linens, Oven, Pets OK, Shower, Swimming Pool, TV, Toaster, VCR, Wireless Internet Access & more amenities »
Activities:Beach

Description: Why rent 12 Bob White Drive in Water Mill summer of 2015? r nSecluded location only 15 minutes from villages of Sag Harbor, Bridgehampton, closeness to Southampton beaches without the traffic [15 minutes] r ... more details »
123...20
Showing 20 of about 395