Holiday rentals in Derby

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Top-rated holiday rentals in Derby

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Top guest favourite
A spacious studio layout includes a cozy queen bed adorned with a geometric quilt. Nearby, a comfortable seating area features a patterned sofa and a green chair. Natural light flows through large windows adorned with bamboo shades, illuminating the warm wood floor.
Flat in Milford
4.95 out of 5 average rating, 187 reviews

The Boathouse, private downtown Harborside suite

The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

Guest favourite
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
4.74 out of 5 average rating, 518 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

A deck overlooking the Housatonic River features a circular table surrounded by four white chairs. A red umbrella stands upright, providing shade. The tranquil water reflects the greenery of the shoreline and the partly cloudy sky.
Bungalow in Seymour
4.7 out of 5 average rating, 137 reviews

Beautiful Waterfront on Housatonic River

Escape & enjoy the views of the mountains & the Housatonic River. Our waterfront little ranch house is great for a relaxing stay in Connecticut. The deck is right across the road down the stairs. Road can be busy at times. The fishing is epic, the sunset views are killer, & the kayaking is refreshing! You have private access to our deck & our 2 sit-in kayaks located across the road. Please be cautious when crossing the road. There are many fun activities/areas to visit nearby like Lake Zoar!

Top guest favourite
The studio features a neatly arranged sleeping area with a quilted bedspread in blue and white patterns. A desk with a chair is positioned nearby, allowing for a focused workspace. Natural light streams through sheer curtains, creating a bright and welcoming ambiance.
Home in Bridgeport
4.93 out of 5 average rating, 41 reviews

Cozy Studio in Bridgeport

Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay

Guest favourite
A cozy sleeping area features a spacious bed centered against a wooden wall unit with built-in shelves. Soft bed linens in muted colors are arranged neatly, with decorative pillows adding a touch of style. Nightstands on either side hold elegant lamps that softly illuminate the space.
Flat in Edgewood
4.95 out of 5 average rating, 501 reviews

Urban Garden Suite

Relax & Recharge in Westville’s Hidden Gem in. We Haven✨ Unwind in this serene, sun-filled, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. 💫 Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

Superhost
A spacious lower-level room features a large bed, a sofa bed, and a dining area with a table and chairs. The brick accent wall adds character, while the tiled floor complements the functional layout. A work desk with a desktop computer is also present.
Private room in Stratford
4.88 out of 5 average rating, 162 reviews

Business or Weekend escape*

This beautiful cozy space can accommodate up to four people. Large bed is and sofa bed are big enough for two people each. There is a large room, private entrance, full bathroom, and the following are free for use: desktop computer, Arcade XL (fully loaded with 20 games), 70 inch TV with blasting sound system, Keurig machine with assortment coffees, teas, snacks, drinking water bottles and sodas. Located conveniently a minute away from Route 95 on exit 31 in Stratford, CT.

Superhost
The exterior of the Courtyard by Marriott Shelton is showcased, featuring a modern, multi-story structure with large windows. The entrance is prominent, framed by landscaped greenery and a spacious parking area. The building is complemented by soft evening lighting.
Hotel room in Shelton
4.81 out of 5 average rating, 113 reviews

Close to Yale University + The Bistro. Pool. Gym.

Settle into comfort at Courtyard by Marriott Shelton, located near I-95 with easy access to Yale, Downtown New Haven, and area parks. Fuel up with Starbucks® drinks at The Bistro, unwind in the indoor pool, or stay productive in the 24/7 fitness center. Free parking and Wi-Fi keep things simple, while nearby hiking trails, restaurants, and local attractions make it easy to explore. Whether you're in town for work or a weekend escape, this stay makes it feel effortless.

Top guest favourite
Private room in West Haven
4.94 out of 5 average rating, 233 reviews

Cozy bedroom near the beach.

The community is calm day and night. The people are very inclusive, diverse, and accepting. Shared living quarters: Living room Kitchen Dinning room Balcony Amenities include: Parking Central AC/ heating Wi-fi Washer & dryer Local benefits: 3 miles away from Yale 2 miles from the University of New Haven 10 min. Walk to Metro North train that can take you to Grand Central 5 min. Walk to grocery store 5 min. Drive to local beach

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, 307 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 cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guest house in Westville
4.92 out of 5 average rating, 329 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

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
4.91 out of 5 average rating, 140 reviews

Midcentury Lakeside Guest Suite

Private guest 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.

Top guest favourite
A charming yellow house is framed by vibrant flowerbeds, showcasing a variety of colorful blooms. The property features a clean, white fence and a pathway leading to a blue front door. Solar panels are installed on the roof, reflecting a commitment to sustainability.
Private room in Hamden
4.97 out of 5 average rating, 503 reviews

Spacious room with private bathroom

You will have a very large room and a private bathroom. The window by the desk overlooks my beehives. You can easily walk down the quiet sidewalk to Whitney Avenue where you'll find restaurants, bars, and public transportation. Two miles to Quinnipiac and Sleeping Giant State Park, a short drive or bus ride to downtown New Haven.

Popular amenities for Derby holiday rentals