Holiday rentals in Derby

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Top-rated holiday rentals in Derby

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
An open bedroom suite is featured, with a warm-colored comforter covering a spacious bed. A wooden dresser stands beside the bed, and a leather couch is positioned against the wall. Natural light enters through windows, brightening the neutral-toned walls.
Guest suite in Ansonia
4.75 out of 5 average rating, 568 reviews

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

Guest favourite
A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.
Cottage in Milford
4.88 out of 5 average rating, 109 reviews

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Top guest favourite
A spacious back deck is displayed, featuring a dining set with an umbrella and additional seating. A small pergola is visible, offering shade. The exterior of the house shows a light-colored siding with several windows, seamlessly blending with the surrounding greenery.
Home in Stratford
4.98 out of 5 average rating, 62 reviews

Charming Folk Victorian Home

This spacious and beautiful Folk Victorian style farmhouse was built in 1917. This home has been updated to include all the modern-day necessities but still has all the charm of a 100 plus year old home! This home is truly the best of the best when it comes to location on the Golden Coast. Whether you are here to visit Fairfield County, New Haven County, or even NYC, you will find this home is close to everything! We are minutes from I-95, Route 15, Route 8, and Metro North Train Station!

Guest favourite
Home in Shelton
4.96 out of 5 average rating, 25 reviews

Shelton's New England Nest: 2 bed EV, Shower, W/D

Discover your perfect Shelton getaway at the New England Nest! This stylish, modern home offers a spacious, airy setting ideal for families and professionals. Stay cool with central AC and enjoy gleaming new hardwood floors and a stunning, fully renovated kitchen. It’s a welcoming, child-friendly environment with room to relax. Enjoy ultimate convenience with in-unit laundry and a major bonus for travelers: a dedicated Universal EV charger on site for your comfortable and connected CT stay.

Top guest favourite
A tranquil view of Swan Lake is captured, surrounded by autumn foliage. Colorful outdoor chairs are positioned on a leaf-covered shore. Sunlight reflects off the calm water, creating a serene atmosphere that invites relaxation.
Home in Oxford
4.97 out of 5 average rating, 78 reviews

Lakefront Summer Oasis - kayak, fish and get cozy!

Relax with family and friends at this breathtaking lake front home. Peaceful setting with beautiful views of Swan Lake. Updated bedrooms, completely renovated bathrooms and all new kitchen appliances. A kayak and paddleboard await your next adventure. A brand new dock was installed for boating, fishing and swimming right from our backyard. Just a few minutes from the town center grocery store, restaurants, amusement parks, skiing and more. Dogs considered on a case by case basis!

Guest favourite
Home in Ansonia
5.0 out of 5 average rating, 6 reviews

Cozy & Pet-friendly 2-Bedroom Home

950 sq. ft of living space on the 1st floor in a quiet and completely remodeled home with 10ft ceilings. Large bedrooms with queen beds and 55" smart TVs create the perfect lounging oasis. Spacious kitchen equipped with everything you need to cook as well as a coffee and espresso machine. Living room has 65" smart TV for binge-watching your favorite shows. Convenient on and off street parking and close proximity to shopping, hiking, picnicking. Well-behaved dogs are welcome :)

Top guest favourite
A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.
Cottage in Seymour
4.96 out of 5 average rating, 142 reviews

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

Guest favourite
The exterior of a charming turn-of-the-century farmhouse is displayed, featuring a white facade and a welcoming porch. A red barn is positioned to the right, set against a backdrop of lush green lawn and trees under a clear blue sky.
Flat in Milford
4.86 out of 5 average rating, 306 reviews

The Farmhouse Estate Apartment

Perfect for families & groups! This 3 bed & 1 bath unit is located on the 1st floor of a turn-of-the-century Farmhouse outfitted with modern amenities. The unit has been specifically designed for Airbnb use and has a boutique hotel feel. Enjoy hardwood floors, Queen memory foam mattresses, high ceilings, keypad door lock (no keys needed), central air, private deck & beautiful views of a 1 acre yard with adjacent apple orchard. No parties or events allowed.

Guest favourite
A well-appointed bedroom features a spacious bed with neutral-toned bedding, flanked by two wooden nightstands with lamps. Decorative wall accents and a potted plant enhance the inviting atmosphere. Natural light filters through the window, illuminating the warm hardwood flooring and soft area rug.
Home in New Haven
4.96 out of 5 average rating, 74 reviews

7 Mins drive to Yale | Large fenced yard

Nestled in the charming neighborhood of New Haven, our home offers the perfect blend of tranquility and convenience. You'll enjoy a peaceful retreat surrounded by tree-lined streets, all while being just a stone's throw away from the vibrant energy of Yale University and the cultural richness of New Haven. Explore local parks, dine at renowned restaurants, and discover the city's unique character, all from your cozy home base in New Haven.

Guest favourite
A cozy living room features a leather sofa, an exercise bike, and a central coffee table resting on a patterned rug. A shelf adorned with framed photographs lines the wall, complementing the warm color scheme.
Guest suite in Shelton
4.82 out of 5 average rating, 323 reviews

Super cozy 1 BR apt. own entrance, great loc.

Very quiet residential neighborhood, very clean, super cozy apartment with two bedrooms, living room; computer desk with work station, kitchenette (no stove), own bathroom, and amenities. 20 minutes away from Bridgeport, 15 minutes away from Yale, New Haven. Lakes in walking distance, Metro-North rail; 7 minutes, local shopping area 1 mile. Bus route in walking distance. Great neighborhood!! All are welcomed. Warm community.

Guest favourite
A spacious living area features large windows allowing natural light to fill the room. A sectional sofa and armchair are arranged around a decorative rug. A television is positioned on a wooden cabinet, and a plant adds a touch of greenery to the decor.
Flat in East Rock
4.93 out of 5 average rating, 135 reviews

Apartment in New Haven

This is a luxurious and spacious apartment on the ground floor of a historic home, centrally located in the heart of East Rock. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The master bedroom has a king bed and a private shower/bathroom. The guest bedroom has a queen bed and library.

Superhost
Flat in Seymour
5.0 out of 5 average rating, 6 reviews

beautiful Cozy 1BR Apt near New Haven

Cozy and modern apartment located on the second floor of a quiet two-family home in Seymour, just 15 minutes from New Haven. features stylish décor, a comfortable bedroom. Only steps from the scenic Housatonic River, the apartment offers the perfect balance of relaxation and convenience. Ideal for guests seeking comfort, charm, and a great location in southern Connecticut.

Popular amenities for Derby holiday rentals