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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Derby

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

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
Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (42)
"Loved our stay. We'll be back I am sure."
The price is AU$475
includes taxes & fees
31 Aug - 1 Sept
Adorable 1-Bedroom Cottage in Weston, CT
Beachfront cottage located in the heart of Fairfield Beach!!
Outdoor dining

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (15)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

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
Westport "Gold Coast" across from Southport beach
Exterior

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (91)
"Fantastic place, location with great host. Highly recommended "
Westport "Gold Coast" across from Southport beach
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!
Direct waterfront cottage on private sandy beach
Exterior

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
Charming 3 Bedroom Beach Front Cottage
Outdoor dining

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) | Interior

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
Exterior

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
Beach cottage on private beach!
Exterior

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Beachside Branford- walk to Beach, Grill
Exterior

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
Waterfront Cottage in Branford
Property grounds

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
Property grounds

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (19)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation
Beachfront Connecticut Retreat w/ Views!
Exterior

Beachfront Connecticut Retreat w/ Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot on the ocean with an amazing host!"
Beachfront Connecticut Retreat w/ Views!
Charming Connecticut Retreat Near Museums & Hiking
House (3 Bedrooms) | Interior

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
Property grounds

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 AU$1,159
includes taxes & fees
11 Aug - 12 Aug
The Island Sound: Ocean View Cottage near Yale, Beach, Downtown, Hikes
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!
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!
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Beach nearby

Renovated Milford Beach home by Charles Island/Silver Sands Pk

10.0 out of 10, Exceptional, (4)
"This place was perfection for my mom and I. The location was easy to get to from highway, the inside of the place was spotless, updated and cozy and property owner Susana was highly responsive to any questions we had. The location was ideal for walks both on the beach and on walking paths. We will definitely stay again in the future. "
Renovated Milford Beach home by Charles Island/Silver Sands Pk
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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Frequently asked questions

What is there to do in Derby near my cottage?
Derby has enough experiences to keep you on the go for weeks (or months!), starting with Walnut Beach. Silver Sands State Park, Shubert Theatre and Sandy Point Beach are other terrific attractions. If you're lingering longer, Yale University Art Gallery and Seabluff Beach are great additions to your itinerary.