
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.

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
LocationValueComfort
4.75 out of 5 average rating, 572 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!
ValueFamilyBackyard
4.97 out of 5 average rating, 650 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.
ValueFamilyDecor
4.88 out of 5 average rating, 109 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.
FamilyLocationCleanliness
4.96 out of 5 average rating, 26 reviews
The ARLO - Walk to Brewery & Restaurants
Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95
FamilyLocationHospitality
4.99 out of 5 average rating, 194 reviews
Luxurious 3BR Apartment w/ Parking & Gym
Our prime location meets modern elegance. This three-bedroom spacious apartment is designed for comfort, convenience, and sophistication in the heart of a dynamic urban community. Whether planning a quiet night in or a lively evening downtown, Hyatus amenities elevate your living experience. º Rooftop Sky Lounge with an outdoor TV º Screening area º Cabanas º Billiards º Bocce courts º Fireside lounge º Co-working space featuring private work pods º Meeting rooms º Cappuccino Bar
FamilyLocationTV
4.95 out of 5 average rating, 127 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!
LocationFamilyComfort
4.97 out of 5 average rating, 79 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 :)
LocationValueLong stay
5.0 out of 5 average rating, 6 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.
LocationFamilyCondition
4.97 out of 5 average rating, 149 reviews
Westville Hideaway | Stylish Guesthouse + Parking
Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.
LocationValueWalkability
4.92 out of 5 average rating, 356 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.
FamilyLocationIndoor spaces
4.82 out of 5 average rating, 325 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.
LocationNearbyComfort
5.0 out of 5 average rating, 6 reviewsPopular amenities for Derby holiday rentals
Other great holiday rentals in Derby

The Salty Porch
FamilyLocationCleanliness
5.0 out of 5 average rating, 56 reviews
7 Mins drive to Yale | Large fenced yard
FamilyLocationQuiet
4.96 out of 5 average rating, 76 reviews
Salt & Blue | Walk to Beach & Tyde •4BR• Fire Pit
FamilyLocationParking
5.0 out of 5 average rating, 31 reviews
Fully furnished 2nd floor apt. 4 rooms 2 bedrooms
FamilyValueNearby
4.88 out of 5 average rating, 84 reviews
Welcome to Ocean’s 55 !
FamilyLocationCondition
4.97 out of 5 average rating, 119 reviews
Cozy 1BR • Wi-Fi • W/D &Yard • Near Griffin & Rt 8
FamilyLocationCleanliness
4.88 out of 5 average rating, 16 reviews
Spacious/Peaceful River View Home For Lg Families
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 9 reviews
Spacious Renovated 3 bedroom near GriffinHospital
ValueLocationAir conditioning
4.66 out of 5 average rating, 163 reviewsDestinations to explore
- Yale University
- Bear Mountain State Park
- Cooper's Beach, Southampton
- Fairfield Beach
- Thunder Ridge Ski Area
- Southampton Beach
- Sunken Meadow State Park
- Soundview Beach
- Kent Falls State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Mohawk Mountain Ski Area
- Robert Moses State Park Beach
- Wölffer Estate Vineyard
- Sleeping Giant State Park
- Millbrook Vineyards & Winery
- Sherwood Island State Park
- Ski Sundown
- Meschutt Beach
- Orient Beach State Park
- Benmarl Winery
- Wesleyan University
- Long Island Aquarium





