Derby Holiday Rentals

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Holiday Rentals in Derby

Apartment in West New Haven

2.0 star property
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
The price is AU$199
includes taxes & fees
7 Dec - 8 Dec
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Apartment in Cheshire

9.2 out of 10, Wonderful, (12)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Downtown Bridgeport

10.0 out of 10, Exceptional, (2)
"Ricardo’s place was perfect for our needs! A small, clean and cozy place, not far from our daytime destination, the apartment offers all the basics - kitchenette, nice bathroom and modern shower, a comfy Queen Size bed, and even some snacks and essentials for a comfortable stay. The area has some restraunts and bars nearby too, though we were happy to stay in and watch some Netflix. I would highly recommend this apartment to a friend, and Ricardo has been a pleasure. Thanks so much!"
United States
Anonymous traveller
The price is AU$251
includes taxes & fees
7 Dec - 8 Dec
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Holiday Home in East Rock

9.0 out of 10, Wonderful, (8)
"the apartment was so beautiful, clean, and spacious! it was a great area to be in! the beds were SUPER comfortable as well, highlight of my trip!"
United States
milly s.
The price is AU$575
includes taxes & fees
7 Dec - 8 Dec
Orange Oasis in East Rock |Free Parking| Near Yale and DT|Large Memory Foam Beds

Apartment in West New Haven

10.0 out of 10, Exceptional, (2)
"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 AU$362
includes taxes & fees
8 Dec - 9 Dec
Westville Stay • 2BR • Near Yale • Free Parking

Apartment in Southbury

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 AU$190
includes taxes & fees
15 Dec - 16 Dec
New One Bedroom Apartment Centrally Located in Southbury

Apartment in East Rock

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.
The price is AU$410
includes taxes & fees
8 Dec - 9 Dec
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Apartment in West New Haven

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 AU$360
includes taxes & fees
7 Dec - 8 Dec
The Nest At Elm City Flats.

Apartment in Fairfield

3.0 star property
9.0 out of 10, Wonderful, (77)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Holiday Home in Wallingford Center

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 AU$441
includes taxes & fees
6 Dec - 7 Dec
Once the old Schools house now a newly furnished Apartment

Holiday Home in Stratford

9.2 out of 10, Wonderful, (51)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is AU$225
includes taxes & fees
1 Jan - 2 Jan 2026
Business or Weekend escape

Apartment in West End - West Side

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 AU$441
includes taxes & fees
7 Dec - 8 Dec
Renovated 2BR Retreat / Modern Comforts Included

Apartment in Ansonia

10.0 out of 10, Exceptional, (1)
"Good location and great landlords."
United States
Ricardo S.
The price is AU$477
includes taxes & fees
6 Dec - 7 Dec
Renovated 2 bedroom entire apartment w/parking

Apartment in West Haven

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 AU$513
includes taxes & fees
7 Dec - 8 Dec
Angelica’s safe haven @ west haven

Apartment in Watertown

9.0 out of 10, Wonderful, (8)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AU$188
includes taxes & fees
7 Dec - 8 Dec
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Apartment in Dwight

8.0 out of 10, Very good, (2)
"The studio apartment is in a very convenient location. It is a lovely walk to Yale. Many restaurants just outside the door. My friends, who joined me for a meal, found parking easily. It was a plus having use of a parking pass for Dwight Street. We never had a problem getting a parking spot. We also loved being able to bring our two small pups with us. The bottle of wine was a thoughtful touch. "
United States
ELIZABETH M S M.
The price is AU$315
includes taxes & fees
6 Dec - 7 Dec
Studio City Stay in the heart of Downtown New Haven, commutable and walkable to Yale and Yale hospital.

Apartment in Dwight

10.0 out of 10, Exceptional, (1)
"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "
United States
Kimberly S.
The price is AU$446
includes taxes & fees
7 Dec - 8 Dec
Cozy Two Bedroom Stay In Downtown New Haven!

Holiday Home in East Rock

9.6 out of 10, Exceptional, (8)
"Property owner takes great care of the place. Instructions were easy to follow and the location was right down the road from the places we were going to. We would rent again if we ever come back to New Haven"
United States
Derek L.
The price is AU$514
includes taxes & fees
10 Dec - 11 Dec
Cozy Gem in Heart of East Rock |King Bed| Near DT and Yale | Free Parking

Apartment in Southbury

9.4 out of 10, Exceptional, (6)
"Great stay. Clean, open space, easy access, and a nice pond in back to bring the dog. Would come back again."
United States
Rooster D.
The price is AU$429
includes taxes & fees
7 Dec - 8 Dec
Private Apartment in Southbury 101

Apartment in Wallingford

10.0 out of 10, Exceptional, (2)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is AU$441
includes taxes & fees
8 Dec - 9 Dec
Newly Remodeled with deck. Close to town center
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 favourite 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 depend 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 AU$225 per night. Entering your travel dates in the search wizard might find you 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?

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit: 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 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, an arcade/games room and 1 hot tub so that you can immerse yourself in your holiday.

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, Osborne Homestead Museum and Osborndale State Park 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.