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Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

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

Beachside Branford- walk t0 Beach, Grill, Fire Pit
Dining

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!
TV

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!
Cozy 2-bedroom Cottage with Access to Bantam Lake
TV, fireplace

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (17)
"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "
Cozy 2-bedroom Cottage with Access to Bantam Lake
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
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior

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

9.6 out of 10, Exceptional, (5)
"The house on the lake is clean and very cute. A few things to keep in mind… The stairs to the loft are VERY steep and VERY narrow. So both adults and small children may struggle to get up and down, especially with any type of luggage. There are no closets or dressers for your clothes so maybe bring hangers and a hook for behind the door. Everything else was perfect. "
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Beach nearby, beach towels

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
On the beach, sun loungers, beach towels

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
Property grounds

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
Miscellaneous

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
On the beach, sun loungers, beach towels

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 SAR 705
SAR 2,093 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
Miscellaneous

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood
1930s Waterfront Cottage on Tuttle's Point
Beach nearby, sun loungers

1930s Waterfront Cottage on Tuttle's Point

9.8 out of 10, Exceptional, (28)
"Tuttles Point is a hidden gem of a neighborhood. I spent my summers as a child in this neighborhood, and I wanted to share my love for this area with my family. This cottage was perfect for what we needed. The view is beautiful and there is so much character in the home that you forget that you might be missing some of our modern comforts. My children loved the rocks out back, the beaches and all the activities in close proximity to this home. If you’re looking for a place to disconnect m,...
1930s Waterfront Cottage on Tuttle's Point
Money Island Home w/ Deck, Kayak & Paddleboards!
Terrace/patio

Money Island Home w/ Deck, Kayak & Paddleboards!

10.0 out of 10, Exceptional, (15)
"This waterfront property has it all! A comfortable, well-appointed, modern, light-filled space designed to take full advantage of its location on a point. Sweeping views of the Sound and other Thimbles from a generous deck perfectly positioned for privacy. The nearby sandbar beach feels almost like your own and the sense of friendly community on this small island is evident. The owners are gracious, welcoming, and immediately attentive to every question or need. Cannot recommend more highly!"
Money Island Home w/ Deck, Kayak & Paddleboards!
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
Charming 3 Bedroom Beach Front Cottage
Outdoor dining

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (2)
"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
Bright Milford Beach House w/ Outdoor Shower
Interior

Bright Milford Beach House w/ Outdoor Shower

3.0 star property
Bright Milford Beach House w/ Outdoor Shower
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

New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

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
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

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.