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Search Cheshire Cottage Rentals from CA $459

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Aug 15 - Aug 17
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Sep 5 - Sep 7
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Browse Select Cheshire Cottages

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Enjoy a peaceful lakeside retreat with a dock, table, and chairs, surrounded by lush grass and a shaded tree.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (35)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Beachside Branford- walk to Beach, Grill
Dining

Beachside Branford- walk to Beach, Grill

9.8 out of 10, Exceptional, (6)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk to Beach, Grill
Direct waterfront cottage on private sandy beach
Guests can enjoy a serene beach scene with a clear view of the ocean and a nearby lighthouse.

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (5)
"Enjoyed our stay very much. Cute cottage, rustic. Only downside was the airport is close "
Direct waterfront cottage on private sandy beach
Historic Whitneyville Cottage
Compact kitchen with a stainless steel refrigerator, double sink, and oven, complete with white cabinetry and a countertop.

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (16)
"My wife and I, and our little dog, had a great experience staying at the Yellow Cottage. For our needs, it was perfectly located. It's on a busy street, but the traffic noises wound down at night. Much nicer than the hotels in the area."
Historic Whitneyville Cottage
Cozy 2-bedroom Cottage with Access to Bantam Lake
Stroll through the lush garden, surrounded by vibrant greenery and colorful flowers, to a serene outdoor space with a wooden fence and inviting bench.

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Guilford Carriage House at Granite Lodge!
Relax in this spacious living area with a high ceiling and exposed beams, featuring a large sofa and armchair, wooden coffee table, and dining area.

Guilford Carriage House at Granite Lodge!

3.0 star property
9.0 out of 10, Wonderful, (2)
"I’m normally not one to leave reviews but I had to for The Carriage House! Everything from the homey, relaxing feel to the great views was amazing! My friends and I wanted to extend our stay lol. We’re already planning another stay here for a summer trip! Also appreciated the host’s friendliness and ensuring we had an enjoyable experience. 10/10"
Guilford Carriage House at Granite Lodge!
Cozy Home near private beach , close to New Haven area colleges Hospitals
Relax in this serene outdoor seating area with a bird-patterned cushion and a vase of fresh flowers.

Cozy Home near private beach , close to New Haven area colleges Hospitals

9.6 out of 10, Exceptional, (64)
"Joel was terrific, very responsive. The “cozy cottage” was everything we were expecting and hoping for. We plan to return."
Cozy Home near private beach , close to New Haven area colleges Hospitals
Charming 3 Bedroom Beach Front Cottage
Enjoy al fresco dining with a view of the ocean from this deck, featuring a table, chairs, umbrella, and grill.

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
Charming 3 Bedroom Beach Front Cottage
New Haven Gem w/ Private Pool, Walk to Beach!
House (3 Bedrooms) | Front of property

New Haven Gem w/ Private Pool, Walk to Beach!

3.0 star property
New Haven Gem w/ Private Pool, Walk to Beach!
Guest Cottage on Country Estate
Relax in a serene garden setting surrounded by lush plants and a stone wall.

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (41)
"the location and size of cottage were just what we were looking for."
Guest Cottage on Country Estate
1930s Waterfront Cottage on Tuttle's Point
Enjoy cooking in this kitchen with oven and sink, plus ample storage in the cabinets above.

1930s Waterfront Cottage on Tuttle's Point

9.6 out of 10, Exceptional, (29)
"We had a wonderful stay! The kitchen was well outfitted and the beach was perfect for our little grandson. Great kayaking, biking, hiking and of course, eating! Backyard and porch were awesome."
1930s Waterfront Cottage on Tuttle's Point
Waterfront Cottage in Branford
Enjoy a serene view of the water from the comfort of this stylish room, featuring a tufted headboard and a cozy chair.

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (95)
"The house is as-advertised. Charming tucked away costal home that is perfect for families. The house has everything you need for a great stay on the water. Dave was extremely responsive when we had a questions. You can't go wrong here. "
Waterfront Cottage in Branford
The Dream Location for Your Perfect Vacation
Enjoy a room with a sea view, featuring a desk, chair, and comfortable bed with a patterned bedspread. A balcony with a railing offers a view of the ocean.

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (20)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
Charming Connecticut Retreat Near Museums & Hiking
Relax in this inviting living room with a plush sofa, fireplace, and comfortable armchair.

Charming Connecticut Retreat Near Museums & Hiking

3.0 star property
Charming Connecticut Retreat Near Museums & Hiking
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Charming single-story house with a gabled roof and inviting front porch.

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

9.4 out of 10, Exceptional, (10)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
Couples can enjoy romantic moments under a natural canopy of palm trees.

The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes

10.0 out of 10, Exceptional, (3)
"This is a nice spot to enjoy the Long Island Sound."
The price is CA $459
CA $1,022 total
includes taxes & fees
Aug 11 - Aug 12
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Enjoy cooking in this kitchen with a sleek island, stainless steel appliances, and a large window.

Upscale Waterbury Retreat w/ Indoor Hot Tub!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Elegant Middlefield Getaway w/ Game Room!
House (4 Bedrooms) | Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Modern Terryville Cottage w/ Deck & Lake View!
Enjoy meals in the fully equipped kitchen with a dining area featuring a round table and range hood.

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Couples can enjoy a romantic beachside moment with a stunning ocean view.

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

9.8 out of 10, Exceptional, (11)
"We loved our stay in this charming beach home! It was spotlessly clean; located in a quiet neighborhood very near Long Island Sound and great shoreline walks; well provisioned and furnished; and offered easy access to the Yale campus and museums as well as an array of interesting restaurants. Our contact, Tom, was a dream to work with: responsive, considerate and informative. We highly recommend this property for anyone visiting the greater New Haven area. "
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Madeline at the front desk and all staff are very welcoming and professional. Hot breakfast is good and accomodations are clean and comfortable. GPS guided me into adjacent parking lot not affiliated with the hotel."
Efrain 1-night trip
Posted 16 hours ago
The Capitol Hotel