Holiday rentals in Derby

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!

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

Cozy, Private Tiny Home Suite for Solo Travelers

This is a private suite in the tiny house mode that offers all you need to stay in cozy comfort, with your own entrance. It becomes your sweet home away from home as you enjoy its modern and convenient features and its bright, open space. Located in a very walkable city, close to amenities and services, area businesses, hospitals, universities, restaurants, and shopping, it's ideal for solo visitors coming to explore, to visit family, or for local work opportunities. Sorry, too small for pets

Perch, for work or wandering the Litchfield Hills.

Welcome to The Perch -- brand new for 2025! Cozy, unique, and private 2nd-floor apartment in a peaceful, rural setting near 84, hiking trails, boutique shops, charming restaurants, and a local movie theater. Explore nearby Woodbury for antiques and enjoy vibrant fall foliage and apple-picking season. Fully equipped with all you might need -- ideal for relaxing, remote work, or some time away. Safe & quiet -- perfect for short visits or extended stays. Discounts available for longer bookings.

In-law Private Studio Apartment

Enjoy a stylish experience at this centrally-located studio apartment. Located in the quaint, quiet, and highly desirable Spring Glen neighborhood, it’s short walking distance of city bus line, as well as several local restaurants, cafes, & local entertainment. Centrally located to Yale University & Hospital, Quinnipiac University, SCSU, Albertus Magnus, as well as downtown Hamden & New Haven. The 400 sq ft apartment has a full bed w/ Tempur-Pedic mattress, & couch pulls out into a full bed.

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.

Private 1-Bdrm Apt in West Haven

House is located in quiet neighborhood and centrally located to just about everything you may need.... beaches, restaurants, entertainment, hospitals, colleges, shops via vehicle. Based on your interest and needs in restaurants, food, shops, activities, etc, you can use Google Maps, Yelp, Uber Eats, etc to provide you with several options. Nicely setup one full-sized bed apartment that sleeps two, provides you with privacy and comfort.

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

Bright, Stylish & Cozy Suite

Welcome to your calm and peaceful retreat — a bright, stylish, and cozy suite designed for comfort and relaxation. Enjoy a sunny bedroom filled with natural light and beautiful views that make every morning special. This private space offers a quiet escape from the city buzz, blending modern style with a warm, homey feel. Perfect for those who appreciate calm surroundings, soft sunlight, and a touch of elegance in every corner.

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.

Cozy, Close to Griffin Hospital

Cozy one bedroom apartment. Perfect for 1-2 people. Walking distance to Griffin hospital. Comfortable queen size bed. Bonus room for lounging. Smart TV in the living room. 2 person round table for dining in the kitchen. WiFi available. Smart TV with access to smart apps. Equipped kitchen for cooking. Close to Downtown Shelton, Downtown Derby, and Downtown Ansonia where there are many restaurants Book today :)

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

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.