Derby holiday rentals

We found 536 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Derby that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Derby

Showing deals for:25 Dec - 1 Jan

Open layout living
Enjoy lounging after a long beach day on the sectional looking out at the water
Large comfortable sectional with a 70" smart tv
Fully stocked kitchen with stainless steel appliances and breakfast counter
Exceptional
(10 reviews)

Luxury Beach Oasis with Amazing Panoramic Ocean Views

Milford

8% off
AU$10,318
for 7 nights, 1 home
AU$1,474 per night
includes taxes & fees
Luxury Beach Oasis with Amazing Panoramic Ocean Views
Property grounds
Terrace/patio
Pool
Interior
Exceptional
(5 reviews)

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Trumbull

8% off
AU$14,517
for 7 nights, 1 home
AU$2,074 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Property grounds
Living area
Private kitchen
Interior
Exceptional
(11 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$3,959
for 7 nights, 1 cottage
AU$566 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Living area
Outdoor dining
Living area
Bedroom 2
Exceptional
(8 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,359
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
Silver Sands Beach Getaway
Living Room
Lake View
Living Room
The Kitchen
Exceptional
(16 reviews)

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

New Haven

8% off
AU$3,416
for 7 nights, 1 home
AU$488 per night
includes taxes & fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Exterior
Terrace/patio
Dining
Room
Exceptional
(46 reviews)

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

East Haven

17% off
AU$9,294
for 7 nights, 1 home
AU$1,328 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Entryway Stairs
View of the Pond
Kitchen
Bathroom
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

8% off
AU$2,384
for 7 nights, 1 apartment
AU$341 per night
includes taxes & fees
Private Apartment in Southbury 101
Dining Room
Stairwell to Master
Living Room
Queen Bedroom 2
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

8% off
AU$3,477
for 7 nights, 1 apartment
AU$497 per night
includes taxes & fees
Beach Apartment in Woodmont Milford
Interior
Living area
Interior
Bathroom
Exceptional
(37 reviews)

1 bedroom Cozy, comfy, super clean, great location and own entrance!!

Shelton

7% off
AU$794
for 7 nights, 1 apartment
AU$113 per night
includes taxes & fees
1 bedroom Cozy, comfy, super clean, great location and own entrance!!
Queen Bedroom
Open Concept Living Room, Dining Room, Kitchen
Open Concept Living Room and Kitchen
Dining Room
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

8% off
AU$2,169
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Private Apartment in Southbury 102

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Derby getaway

Enjoy the museums and other features of Derby. One of the city's many top draws is its parks. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Derby

Are you hoping to discover things to do while you're in the area? Venture out of your holiday home and check out everything that makes Derby a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Beardsley Zoo (9 mi / 14.4 km)
  • Quassy Amusement Park (14.6 mi / 23.5 km)
  • Great River Golf Club (3.2 mi / 5.2 km)
  • Yale Golf Course (5.4 mi / 8.7 km)
  • Connecticut Golf Club (13.1 mi / 21.1 km)
  • Blue Jay Orchards (15.9 mi / 25.6 km)

Exploring the natural landscape of Derby

Whether you're looking for adventure or just want to take in the scenery, Derby is a great spot to appreciate mother nature. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Milford Green (7.1 mi / 11.5 km)
  • Gulf Beach (7.9 mi / 12.8 km)
  • Seabluff Beach (8.2 mi / 13.1 km)
  • New Haven Green (8.5 mi / 13.7 km)
  • Silver Sands (8.5 mi / 13.7 km)
  • Beacon Falls Town Recreation Field (8.5 mi / 13.8 km)

Transport options to and around Derby

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 10.9 mi (17.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 11.2 mi (18 km) away.

Frequently asked questions

What is the best area to stay in Derby when booking a holiday rental?
When considering a holiday rental in Derby, Connecticut, a popular area to stay is the charming downtown district. This area is not only convenient but also rich in local culture and community spirit. You'll find a variety of properties available, ranging from quaint apartments to larger family homes, suiting different preferences and budgets.The downtown area is home to several attractions, including the picturesque Derby Greenway, which offers scenic walking and cycling paths, great for exploring the natural beauty of the region. Additionally, the historic Derby Historical Society provides fascinating insights into the town's past, making it a great spot for those interested in local history.Another appealing option is the neighbourhood near the Housatonic River. This area features lovely waterfront views and is close to parks where you can enjoy outdoor activities. Staying here allows easy access to the river, providing opportunities for fishing, kayaking, and picnicking along the banks.
What is the most popular type of holiday rental accomodation in Derby?
In Derby, apartments are the predominant type of holiday rental, with several available throughout the area. These apartments typically provide modern amenities such as fully equipped kitchens, spacious living areas, and comfortable bedrooms, making them a convenient choice for travellers. Many units also feature additional comforts like laundry facilities and parking, suiting the needs of both short-term and longer stays.
Are there any family house rentals in Derby?
In Derby, Connecticut, there are several family-friendly house rentals available, making it a suitable destination for groups looking to enjoy a comfortable stay. Properties in this area often feature spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where children can play safely. Many homes also come with amenities such as Wi-Fi and laundry facilities to enhance convenience during your visit.Visitors can explore the local parks, such as Osbornedale State Park, which offers trails for hiking and picnic spots. The proximity to the Housatonic River adds opportunities for outdoor activities, including fishing and kayaking.
What are popular rental amenities in Derby?
In Derby, popular holiday rental amenities typically include features that enhance comfort and convenience for travellers. Many rentals come equipped with kitchens, allowing guests to prepare their own meals, which is especially beneficial for families or those planning longer stays. Additionally, most properties offer a balcony, providing a pleasant outdoor space to relax and enjoy the surroundings. For added flexibility, many units also have a sofa bed, accommodating extra guests without the need for additional bedrooms. Onsite parking is another common amenity, making it convenient for those travelling by car.
When is the best time to visit Derby for a holiday rental?
July marks the peak travel season in Derby, Connecticut, attracting visitors eager to enjoy the warm summer weather and vibrant local events. From July to September, the area becomes a hub of activity, with families and adventure seekers taking advantage of outdoor recreational options, such as kayaking on the Housatonic River or exploring the scenic parks nearby.During July, you can expect temperatures typically ranging from 20 to 30 degrees Celsius, providing a pleasant climate for outdoor activities and sightseeing. This is also when Derby hosts various festivals, making it an exciting time to experience the local culture and community spirit.For those looking for a more budget-friendly option, December presents a lovely opportunity to visit Derby. While this is considered the low season, the charm of the town during the winter months, complete with holiday decorations and a cozy atmosphere, can offer a unique and enjoyable experience.Ultimately, the best time to visit Derby for a holiday rental depends on your preferences.
What are the top attractions in Derby?
In Derby, Connecticut, visitors can explore a variety of attractions that showcase the town's rich history and natural beauty. The Derby Historical Society offers insights into the local heritage, featuring exhibits and events that highlight the area's past. Nearby, the beautiful Osbornedale State Park is great for outdoor enthusiasts, with trails for hiking and picturesque spots for picnicking.For those interested in recreational activities, the Derby Greenway provides a scenic pathway ideal for walking, running, or cycling, connecting Derby to surrounding areas. The city's proximity to the Housatonic River also allows for opportunities to engage in fishing and kayaking.Additionally, the downtown area features charming shops and eateries, giving visitors a taste of local culture.
Are all fees included in the Derby holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Derby holiday homes with parking?
Stayz offers a wide selection of holiday homes in Derby with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Derby holiday homes?
You can find great discounts on holiday homes in Derby on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Derby holiday home booking on Stayz?
To find Derby holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Derby?
A long-stay holiday home in Derby is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Derby holiday home?
Book your Derby holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Derby?
Prices for holiday homes in Derby vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Derby to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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