A wooden bridge over a river, surrounded by lush green trees and large rocks.

Derby Vacation Rentals

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Our top choices for Derby vacation rentals

Near Yale & Lighthouse Point Beach: Home w/ Pool!

Near Yale & Lighthouse Point Beach: Home w/ Pool!
3.0 star property
East Shore
The price is CA $561
CA $1,014 total
includes taxes & fees
Jul 8 - Jul 9
Near Yale & Lighthouse Point Beach: Home w/ Pool!

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is CA $888
CA $1,518 total
includes taxes & fees
Jul 2 - Jul 3
Beechmont - Perfect for Family Retreat!

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is CA $279
CA $407 total
includes taxes & fees
Jul 26 - Jul 27
DUNE Fairfield Beach

Elite room stay

Elite room stay
Bridgeport
The price is CA $294
CA $488 total
includes taxes & fees
Jul 2 - Jul 3
Elite room stay

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is CA $185
CA $467 total
includes taxes & fees
Jul 2 - Jul 3
Angelica’s safe haven @ west haven

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is CA $816
CA $1,412 total
includes taxes & fees
Jul 8 - Jul 9
Clear LI Sound waterview, Wedding pics, Yale&Beach

Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is CA $337
CA $802 total
includes taxes & fees
Jul 2 - Jul 3
Coastal Landing Stay

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
9.0 out of 10, Wonderful, (2 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
The price is CA $606
CA $1,059 total
includes taxes & fees
Jul 13 - Jul 14
#43- Modern Luxury Log Cabin Retreat | Fire Pit

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk
Downtown Bridgeport
9.8 out of 10, Exceptional, (13 reviews)
"I was surprised by the large size of this apt, and that it had everything I needed for my stay. The location was perfect and very close to the event I was there for. Excellent host and I'm looking forward to booking this place again next year."
United States
Shamel
The price is CA $199
CA $328 total
includes taxes & fees
Jul 12 - Jul 13
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is CA $168
CA $418 total
includes taxes & fees
Jul 5 - Jul 6
Once the old Schools house now a newly furnished Apartment

4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is CA $734
CA $1,084 total
includes taxes & fees
Jul 5 - Jul 6
4 Mi to Beach & Dtwn! Charming Fairfield Home

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is CA $124
CA $278 total
includes taxes & fees
Jul 8 - Jul 9
One bedroom in United States of America, New Haven

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
East Rock
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is CA $327
CA $721 total
includes taxes & fees
Jul 6 - Jul 7
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale

Beautiful Downtown New Haven Retreat

Beautiful Downtown New Haven Retreat
Downtown New Haven
The price is CA $169
CA $461 total
includes taxes & fees
Jul 5 - Jul 6
Beautiful Downtown New Haven Retreat

Near Yale & Lighthouse Point Beach: Home w/ Pool!

Near Yale & Lighthouse Point Beach: Home w/ Pool!
East Shore
9.6 out of 10, Exceptional, (10 reviews)
"Perfect family getaway - quiet area for young family. House is well equipped and in excellent condition. "
United States
Catherine G.
The price is CA $467
CA $1,018 total
includes taxes & fees
Jul 8 - Jul 9
Near Yale & Lighthouse Point Beach: Home w/ Pool!

Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is CA $168
CA $418 total
includes taxes & fees
Jul 22 - Jul 23
Fully Furnished 1BR Apartment

Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is CA $820
CA $1,109 total
includes taxes & fees
Jul 12 - Jul 13
Heavenly Home in New Haven /5 mins drive from Yale

Beautiful Bayfront Home • Heated Pool & Jacuzzi

Beautiful Bayfront Home • Heated Pool & Jacuzzi
West Haven
The price is CA $1,188
CA $1,803 total
includes taxes & fees
Jul 12 - Jul 13
Beautiful Bayfront Home • Heated Pool & Jacuzzi

Beach Apartment in Woodmont Milford 102

Beach Apartment in Woodmont Milford 102
Milford
The price is CA $307
CA $578 total
includes taxes & fees
Jul 5 - Jul 6
Beach Apartment in Woodmont Milford 102

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.2 out of 10, Wonderful, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is CA $180
CA $304 total
includes taxes & fees
Jul 6 - Jul 7
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Derby. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Derby?

Yes, we offer vacation rentals near top attractions in Derby, or you can go with a secluded option if you'd like a relaxing place to stay. Derby is known for its parks and museums.

What are some of the best vacation rentals in Derby?

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12: Visitors like this Derby vacation home rental. It is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

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 vacation rental in Derby like?

A vacation rental is a private property you can stay in for several days or longer in Derby. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.