Holiday houses 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, 567 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

Superhost
The property features a white two-story house with a covered front porch and lush green landscaping. A red barn stands nearby, contrasting against the blue sky, while a paved driveway leads up to the residence, offering ample space for off-street parking.
Apartment in Milford
4.87 out of 5 average rating, 267 reviews

Renovated Apartment in a Historic Farmhouse Estate

Take-in fresh air and tranquil views from the 2nd floor deck of a 1-acre property with an adjacent apple orchard. Rustic decor mixes with industrial flair to create an inspiring interior that offers country comforts along with modern amenities. Enjoy hardwood floors, Queen memory foam mattresses, high ceilings, keypad door lock (no keys needed), fast Wifi, central air conditioning, & a private deck. We can't wait to host you! This is a multi-unit property, so we do not allow parties or events.

Top Guest favourite
An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.
Apartment in Milford
4.97 out of 5 average rating, 643 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Top Guest favourite
A spacious living area is illuminated by natural light streaming through large windows. A comfortable gray sofa with decorative pillows faces a modern coffee table. A stylish area rug adds color, while a wall-mounted TV and decorative plants enhance the space.
Apartment in New Haven
4.96 out of 5 average rating, 442 reviews

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the heart of New Haven’s historic downtown, our designer home is part of the city’s most prestigious new luxury complex, renowned for its unmatched amenities and design. Highlights: • Prime location just steps from Yale University • Immaculately cleaned before every stay • Complimentary coffee, plush linens, and premium toiletries • 24/7 state-of-the-art fitness center • Expansive rooftop terrace with grills and chic lounges • Over 700 sqft of bright and sophisticated living space

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
Apartment in Southbury
4.97 out of 5 average rating, 107 reviews

Cozy Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to i84

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, 141 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
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
Apartment in New Haven
4.97 out of 5 average rating, 115 reviews

Soaking Tub Retreat | Cozy Luxe Stay Near Yale

Relax in this peaceful retreat just 10 minutes from downtown New Haven and Yale. Ideal for solo travelers or anyone seeking a quiet escape. Enjoy the deep soaking tub, calming decor, fast Wi-Fi, and a serene space to recharge. No parties—just peace, comfort, and good vibes. This is a calm, intentional space for peaceful stays only. We welcome guests who appreciate good energy and quiet rest.

Top Guest favourite
The exterior of the midcentury home is presented among lush greenery, featuring a brown wooden facade and small windows. Vibrant flowering plants in shades of pink and green surround the area, providing a natural frame against the serene backdrop of trees and the nearby lake.
Guest suite in West Haven
4.93 out of 5 average rating, 248 reviews

Midcentury Lakeside Guest Suite

Private guest studio suite in a beautiful, midcentury lakeside home. Built in 1957, this home on a quiet residential street is a unique piece of modern architecture around a serene lake in suburban Connecticut. It is walkable from the nearby railway station, and it is close to West Haven's picturesque beaches, and a short drive from downtown New Haven.

Superhost
A cozy space is highlighted by natural light streaming through multiple windows. Two dogs sit on the hardwood floor between a staircase and a plush area. A potted plant adds a touch of green, while various furnishings are positioned throughout the room.
Home in Shelton
4.83 out of 5 average rating, 116 reviews

Mid-Century Modern House - Ciela Haus

IG: @cielahaus A mid-century modern home with cathedral ceilings, carefully curated interiors and a warming indoor charcoal BBQ. It is the perfect getaway for a group of friends or family to explore the outdoors, farms, wineries or to simply enjoy tranquility. I hope you enjoy staying here as much as I loved renovating, curating and styling it!

Top Guest favourite
A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.
Home in Branford
4.98 out of 5 average rating, 108 reviews

Adorable Beach House on LI Sound

Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream

Popular amenities for Derby holiday rentals