
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.

Amazing views of the Brass City
East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

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

Modern Downtown Stay Near Yale • Rooftop • Gym
Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! With Broadway just around the corner and some of New Haven’s best Pizza a stone’s throw away you’d be hard-pressed to find a better location for your stay. Enjoy cooking up a nice dinner at home one night using the fully-equipped kitchen provided. Spend the evening on the rooftop terrace watching the sunset over the city skyline before tucking in for the night. Use the downstairs gym for a morning workout.

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!

The Pond Mill Retreat w/ 2 Bdrms & Pool
Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Lovely water front lower-level loft, free parking
This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

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

Westville Schoolhouse by Stephanie and Damian
The beautiful "School House" sits in the heart of Westville, New Haven's most artsy and eclectic neighborhood. The "School House" is a 15 minute walk to the Westville Concert bowl, and the Yale Football stadium for an easy commute to a concert or game. Just a one minute walk to the center of Westville you will find Lotta's artist studio, Bella's restaurant, RAWA, Pistachio Coffee and Manjares Tapas & Wine, as well as the famous Camacho Garage restaurant amongst other attractions.

Westshore Luxury
Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.

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.

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.
Popular amenities for Derby holiday rentals
Other great holiday rentals in Derby

Apt Near Yale|Walkable&Cozy/ for Connection & Rest

The Seabreeze

Cozy studio unit

Bright & Cheerful 3 Bed suite w/ Free Parking

Luxe cozy 2br/1ba Milford bungalow-walk to beach!

Waterfront Cottage With Unforgettable Views

Charming 1875 Retreat - Walk to Village

Lakefront Getaway
Destinations to explore
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- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Thunder Ridge Ski Area
- Southampton Beach
- Robert Moses State Park Beach
- Sunken Meadow State Park
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
- Bear Mountain State Park
- Yale University Art Gallery
- Mount Southington Ski Area
- Ski Sundown
- Sherwood Island State Park
- Sleeping Giant State Park
- Compo Beach
- Orient Beach State Park
- Dunewood
- Meschutt Beach
- Benmarl Winery
- Wölffer Estate Vineyard




