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Derby Holiday Rentals

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Our top choices for Derby holiday rentals

9.6 out of 10, Exceptional, (10)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
9.4 out of 10, Exceptional, (8)
"The apartment was very clean with everything we needed for our stay. Outside noise was a little loud so I’d suggest a sound machine, but in case your forget the awesome host has supplied soft ear plugs for you. I would definitely visit again. "
United States
Chrystie
The price is NZ$400
includes taxes & fees
2 Jan - 3 Jan 2026
Orange & Groovy Stylish Amphitheater, Park, Metro North, Ferry All 2-10min walk

Apartment in West End - West Side

Renovated 2BR Retreat / Modern Comforts Included
10.0 out of 10, Exceptional, (2)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is NZ$502
includes taxes & fees
4 Jan - 5 Jan 2026
Renovated 2BR Retreat / Modern Comforts Included
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is NZ$284
includes taxes & fees
5 Jan - 6 Jan 2026
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
10.0 out of 10, Exceptional, (3)
"We were only here for a short stay, but everything was smooth and comfortable for us! Hotel-like linens and blackout curtains made for a very cozy sleeping experience."
United States
ross f.
The price is NZ$412
includes taxes & fees
8 Jan - 9 Jan 2026
Westville Stay • 2BR • Near Yale • Free Parking
10.0 out of 10, Exceptional, (2)
"Apartment was very clean and well supplied, host very responsive. Location is convenient to Yale and restaurants. As noted in the listing, you'll have to carry your luggage up 4 flights of stairs. There is some street noise as is typical for that part of the city. Very happy with it overall and plan to stay again."
United States
Philip S.
The price is NZ$358
includes taxes & fees
23 Dec - 24 Dec
One bedroom apartment in United States of America, New Haven

Apartment in West New Haven

The Nest At Elm City Flats.
9.4 out of 10, Exceptional, (6)
"Nice place! Short but sweet trip. Appreciate how quick your communication was and your accommodations!"
United States
Lori K.
The price is NZ$406
includes taxes & fees
23 Dec - 24 Dec
The Nest At Elm City Flats.

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
The price is NZ$342
includes taxes & fees
23 Dec - 24 Dec
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
3.0 star property
The price is NZ$622
includes taxes & fees
23 Dec - 24 Dec
2 Mi to Beach, Shared Yard Space: West Haven Apt!
10.0 out of 10, Exceptional, (6)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is NZ$559
includes taxes & fees
23 Dec - 24 Dec
Angelica’s safe haven @ west haven
9.4 out of 10, Exceptional, (3)
"Very nice house....loved the front enclosed porch, and the kitchen was amazing with everything we needed. The deck with the Blackstone Grill was a great place to sit and relax. We enjoyed many of the nearby restaurants too. Matt and Jess were great hosts!J&J, Mooresville, NC"
United States
Jena
The price is NZ$641
includes taxes & fees
29 Dec - 30 Dec
The ARLO - Walk to Brewery and Restaurants
10.0 out of 10, Exceptional, (1)
"A very nice, easy, clean upper level unit. Very comfortable and easy to stay. Room for our family move and enjoy the area! "
United States
Chad L.
The price is NZ$549
includes taxes & fees
4 Jan - 5 Jan 2026
Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio
9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is NZ$213
includes taxes & fees
3 Jan - 4 Jan 2026
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Dwight

Yale Casa Verde Studio
9.6 out of 10, Exceptional, (8)
"Had a great stay!"
United States
Jeffrey C.
The price is NZ$354
includes taxes & fees
23 Dec - 24 Dec
Yale Casa Verde Studio

Apartment in Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (12)
"Convenient location. Just off Rte 91. Easy street parking. The studio is as pictured - exposed brick walls, high ceilings. Everything you need for a short stay. "
United States
Lois G.
The price is NZ$313
includes taxes & fees
29 Dec - 30 Dec
Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$501
includes taxes & fees
2 Jan - 3 Jan 2026
Once the old Schools house now a newly furnished Apartment
9.8 out of 10, Exceptional, (19)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
The price is NZ$215
includes taxes & fees
29 Dec - 30 Dec
New One Bedroom Apartment Centrally Located in Southbury
9.6 out of 10, Exceptional, (69)
"The apartment was very clean and convenient. Will definitely stay there again. "
United States
Joan S.
The price is NZ$400
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious 2 Bedroom apartment close to Yale Bowl
10.0 out of 10, Exceptional, (1)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is NZ$357
includes taxes & fees
7 Jan - 8 Jan 2026
Entire guesthouse in Southbury, Connecticut 3 guests1 bedroom2 beds1 bath.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Derby Hotel Reviews

Find out more about Derby

Everything you need to know about Derby holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Derby holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Derby holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Derby holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Derby. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Derby holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Derby holiday rentals we have selected for you start as low as NZ$245 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Derby rentals

At Expedia, we put the best Derby holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Derby rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Derby holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Derby. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Derby?

Yes, there are holiday rentals close to the most popular sights in Derby, or you can select a more secluded option if you're looking for a relaxing stay. Derby is known for its parks and museums.

What are some of the best holiday rentals that Derby has to offer?

Peaceful Vintage Home with Private Pond in Redding, CT.: This holiday home rental outside of Derby is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

What’s there to see and do in Derby?

While exploring the area, visit family-friendly sights like SportsCenter of Connecticut, or get outside and enjoy nature at Housatonic River. While here, Osborndale State Park and Osborne Homestead Museum are other places worth a visit.

What’s a holiday rental in Derby like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Derby. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family getaway.