Search Cottages in Cheshire Historic District

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Check prices for these dates

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2 May - 4 May
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9 May - 11 May
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23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 48 Cottages in Cheshire Historic District with updated reviews, rates, and availability.

Beachside Branford- walk t0 Beach, Grill, Fire Pit
Smart TV

Beachside Branford- walk t0 Beach, Grill, Fire Pit

10.0 out of 10, Exceptional, (3)
"Charming little cottage that was just right for our trip to the CT shoreline."
Beachside Branford- walk t0 Beach, Grill, Fire Pit
Guilford Carriage House at Granite Lodge!
Pool

Guilford Carriage House at Granite Lodge!

10.0 out of 10, Exceptional, (9)
"We had a couple of out of town events in the are this past weekend, and it was also my birthday, so we decided to stay somplace special. The Granite Lodge Carriage hose was all of that! Beautifully decorated and furnished with lots of special touches from the host! We would definitely recommend, and will!"
Guilford Carriage House at Granite Lodge!
Family Friendly Cottage for 8 with Arcade Games!!
Fridge, microwave, oven, stovetop

Family Friendly Cottage for 8 with Arcade Games!!

10.0 out of 10, Exceptional, (4)
"We had a wonderful family Thanksgiving gathering. The space is very open and welcoming. The basement games are a fun addition. The beds were comfortable and the linens of good quality. Nancy was very quick and supportive with any questions we had. Although it's close to the Tweed New Haven airport, we were not bothered by the planes and at night they don't seem to fly. "
Family Friendly Cottage for 8 with Arcade Games!!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (31)
"Stayed here for a work trip for a couple of nights. Very comfortable, quiet, and nice scenery."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Exterior

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

9.6 out of 10, Exceptional, (10)
"A/C was started for us, so it was comfortable."
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
The Dream Location for Your Perfect Vacation
3 bedrooms, desk, free WiFi, bed sheets

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
Direct waterfront cottage on private sandy beach
Exterior

Direct waterfront cottage on private sandy beach

10.0 out of 10, Exceptional, (2)
"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
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.6 out of 10, Exceptional, (14)
"Road noise was annoying. Otherwise as advertised."
Historic Whitneyville Cottage
Guest Cottage on Country Estate
Exterior

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (39)
"Beautiful cottage, spectacular property, wonderful hosts. Not sure what else to say? We came up to CT with our pup to look at areas we may want to move to. The cottage was perfect for us, nice and private and lots of land for our pup to walk. Great state park a few miles away and plenty of good restaurants nearby. Very happy!"
Guest Cottage on Country Estate
Short Beach Coastal Cottage
Property grounds

Short Beach Coastal Cottage

10.0 out of 10, Exceptional, (15)
"It was really evident that the hosts enjoy this project. Very nice people and everything was tip top."
Short Beach Coastal Cottage
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
Property grounds

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

10.0 out of 10, Exceptional, (2)
"This is a nice spot to enjoy the Long Island Sound."
The price is AED 691
AED 2,049 total
includes taxes & fees
28 Apr - 29 Apr
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
Modern Terryville Cottage w/ Deck & Lake View!
Fridge, microwave, stovetop, dishwasher

Modern Terryville Cottage w/ Deck & Lake View!

9.0 out of 10, Wonderful, (4)
"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!
Charming 2-bedroom farm cottage in quiet Killingworth neighborhood
Fridge, microwave, oven, stovetop

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood
Charming Connecticut Retreat Near Museums & Hiking
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, cookware/dishes/utensils

Charming Connecticut Retreat Near Museums & Hiking

3.0 star property
Charming Connecticut Retreat Near Museums & Hiking
Guilford Carriage House at Granite Lodge!
Interior

Guilford Carriage House at Granite Lodge!

3.0 star property
10.0 out of 10, Exceptional, (1)
"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!
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!
Charming West Haven Home - Walk to Beach!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Charming West Haven Home - Walk to Beach!

3.0 star property
Charming West Haven Home - Walk to Beach!
Lakefront Home, Close to Mt Southington!
House (3 Bedrooms) | Interior

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!
Upscale Waterbury Retreat w/ Indoor Hot Tub!
House (3 Bedrooms) | Interior

Upscale Waterbury Retreat w/ Indoor Hot Tub!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Modern Terryville Cottage w/ Deck & Lake View!
Cottage (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
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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Other property types in Cheshire Historic District

New Haven Village Suites
Suite, Multiple Beds | Egyptian cotton sheets, premium bedding, pillowtop beds, desk

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2025)
"Good stay. "
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Furnished Apartments by Hyatus Downtown at Yale
Luxury Apartment, 2 Bedrooms, Kitchen | Private kitchen | Full-size fridge, microwave, oven, stovetop

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (43)
"This was the perfect place for our family to stay while visiting Yale / New Haven. Everything was walkable, the property was great - our teenagers played pool for hours and we used the big screen downstairs to stream movies. Loved it! "
Luxury Furnished Apartments by Hyatus Downtown at Yale
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.