Search Cheshire Historic District Cottage Rentals from CA $272

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Browse Select Cheshire Historic District Cottages

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

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

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

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

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

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

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

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

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

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

3.0 star property
Charming Connecticut Retreat Near Museums & Hiking

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!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!

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

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

Modern Terryville Cottage w/ Deck & Lake View!

9.2 out of 10, Wonderful, (5)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
Modern Terryville Cottage w/ Deck & Lake View!

Cozy Country Cottage

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very accommodating and understanding host.They are warm and willing to listen and make your stay as comfortable as possible. Trent and his family will go out of their way to make the stay memorable.. I would highly recommend the stay at this accommodation to everyone. A home away from home."
The price is CA $272
CA $439 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Country Cottage

Cheerful 3BR Cottage, 5 min walk to Beach!

10.0 out of 10, Exceptional, (1)
"We had a lovely stay here! The house is very cute, has a nice backyard, and is very close to the beach but also just a few minutes drive from food. The neighborhood was quiet and the little park/town beach area was great - easy access to the water, a little playground, and an awesome splash pad! We were very comfortable in the house. They’ve put in lots of different sleeping arrangements, including a daybed on the porch, and the rooms were all clean and comfortable. Jens was wonderful and very...
Cheerful 3BR Cottage, 5 min walk to Beach!

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!
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 Historic District Hotel Reviews