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Woodbridge holiday rentals

We found 563 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Woodbridge to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include Wi-Fi and a hot tub. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Woodbridge

Showing deals for:11 Dec - 18 Dec

Living area
Living area
Property grounds
Private kitchen
Exceptional
(10 reviews)

Renovated Milford Beach home by Charles Island/Silver Sands Pk

Milford

8% off
AU$3,871
for 7 nights, 1 cottage
AU$553 per night
includes taxes & fees
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Pool
Terrace/patio
Dining
Property grounds
Exceptional
(5 reviews)

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

Trumbull

8% off
AU$14,269
for 7 nights, 1 home
AU$2,038 per night
includes taxes & fees
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Dining
Outdoor dining
Interior
Property grounds
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
AU$9,578
for 7 nights, 1 home
AU$1,368 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Terrace/patio
Living area
Living area
Exterior
Exceptional
(16 reviews)

Spacious Modern Beach House, perfect for families

Branford

8% off
AU$6,823
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
Spacious Modern Beach House, perfect for families
Living area
Outdoor dining
Kitchen
Bedroom 2
Exceptional
(8 reviews)

Silver Sands Beach Getaway

Milford

16% off
AU$4,330
for 7 nights, 1 home
AU$619 per night
includes taxes & fees
Silver Sands Beach Getaway
Living area
Interior
Private kitchen
Living area
Excellent
(5 reviews)

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

East Haven

7% off
AU$4,165
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
Dining
Interior
Living area
Room
Very good
(5 reviews)

Family, pet friendly downtown New England charmer. Mins from Yale, Choate, QU.

Wallingford

12% off
AU$3,633
for 7 nights, 1 home
AU$519 per night
includes taxes & fees
Family, pet friendly downtown New England charmer. Mins from Yale, Choate, QU.
Living Room
Lake View
Living Room
The Kitchen
Exceptional
(15 reviews)

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

New Haven

8% off
AU$2,269
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Room
Exterior
Private kitchen
Interior
Exceptional
(18 reviews)

Minutes to Walnut Beach, newly renovated 3 bedroom home

Milford

7% off
AU$1,968
for 7 nights, 1 home
AU$281 per night
includes taxes & fees
Minutes to Walnut Beach, newly renovated 3 bedroom home
Dining
Terrace/patio
Exterior
Living area
Exceptional
(46 reviews)

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

East Haven

17% off
AU$6,092
for 7 nights, 1 home
AU$870 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Dining Room
Stairwell to Master
Living Room
Queen Bedroom 2
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

7% off
AU$2,504
for 7 nights, 1 apartment
AU$358 per night
includes taxes & fees
Beach Apartment in Woodmont Milford
Living area
Your view everyday!
Interior
Living area
Exceptional
(46 reviews)

#2 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk

Milford

8% off
AU$3,312
for 7 nights, 1 apartment
AU$473 per night
includes taxes & fees
#2 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk
Bathroom
View of the Pond
Entryway Stairs
Kitchen
Exceptional
(7 reviews)

Private Apartment in Southbury 101

Southbury

7% off
AU$1,930
for 7 nights, 1 apartment
AU$276 per night
includes taxes & fees
Private Apartment in Southbury 101
Interior
Living area
Interior
Bathroom
Exceptional
(37 reviews)

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

Shelton

7% off
AU$795
for 7 nights, 1 apartment
AU$114 per night
includes taxes & fees
1 bedroom Cozy, comfy, super clean, great location and own entrance!!
Private kitchen
Pool
Living area
Interior
Exceptional
(7 reviews)

Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4

Southbury

8% off
AU$1,728
for 7 nights, 1 apartment
AU$247 per night
includes taxes & fees
Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4
Dining Room
Open Concept Living Room, Dining Room, Kitchen
Open Concept Living Room and Kitchen
Queen Bedroom
Wonderful
(6 reviews)

Private Apartment in Southbury 102

Southbury

8% off
AU$1,725
for 7 nights, 1 apartment
AU$246 per night
includes taxes & fees
Private Apartment in Southbury 102
Exterior
Living area
Living area
Room
Exceptional
(34 reviews)

#1 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk

Milford

8% off
AU$3,787
for 7 nights, 1 apartment
AU$541 per night
includes taxes & fees
#1 Beautiful Milford Beach Right Across Street - Charles Island/Silver Sands Pk

  • 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

Head to the arty city of Woodbridge

Enjoy the art galleries and other features of Woodbridge. This city is well-known for its restaurants and shopping. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Woodbridge

Do you want to find top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Woodbridge has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Beardsley Zoo (13.3 mi / 21.4 km)
  • Quassy Amusement Park (14.1 mi / 22.7 km)
  • Mount Southington Ski Area (16.4 mi / 26.4 km)
  • Powder Ridge Mountain Park and Resort (17.3 mi / 27.8 km)
  • Yale Golf Course (2.6 mi / 4.3 km)
  • Grassy Hill Country Club (6.3 mi / 10.2 km)

Exploring the natural features in Woodbridge

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Woodbridge. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • New Haven Green (5.3 mi / 8.5 km)
  • Beacon Falls Town Recreation Field (7.2 mi / 11.6 km)
  • New Haven Harbor (7.2 mi / 11.6 km)
  • Mount Carmel (7.3 mi / 11.7 km)
  • Oak Street Beach (7.3 mi / 11.8 km)
  • Seabluff Beach (7.4 mi / 11.9 km)

Travelling to and around Woodbridge

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 8.4 mi (13.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 11 mi (17.7 km) away.

Frequently asked questions

What is the best area to stay in Woodbridge when booking a holiday rental?
When considering a holiday rental in Woodbridge, Connecticut, the best area to stay is near the charming centre of town. This neighbourhood offers a delightful blend of suburban tranquillity and easy access to local amenities. With a range of properties available, from quaint cottages to more spacious homes, visitors can find accommodations that suit their preferences.Staying in the heart of Woodbridge places you close to several attractions that showcase the area's natural beauty and cultural offerings. One top highlight is the beautiful West Rock Ridge State Park, which provides stunning hiking trails and scenic views, superb for outdoor enthusiasts. Additionally, the Woodbridge Town Centre offers a variety of shops and restaurants, making it a convenient spot for dining and leisure activities.Another appealing aspect of the area is its proximity to the vibrant city of New Haven, just a short drive away. This allows guests to easily explore attractions such as the renowned Yale University and its captivating art galleries, while still enjoying the peaceful atmosphere of Woodbridge.
What is the most popular type of holiday rental accomodation in Woodbridge?
In Woodbridge, cottages and apartments are the most popular types of holiday rentals, with several options available throughout the area. These accommodations typically feature home-like amenities, including fully equipped kitchens, comfortable living spaces, and outdoor areas for enjoying the peaceful surroundings. Cottages often provide a quaint and rustic charm, while apartments may offer more modern conveniences, making them suitable for various travellers.
Are there any family house rentals in Woodbridge?
In Woodbridge, Connecticut, there are several family-friendly house rentals available. This charming suburb offers spacious rooms, making it an excellent choice for families seeking comfort and convenience. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play.Visitors can explore the local parks, such as the scenic Woodbridge Town Green, which offers playgrounds and walking trails. The nearby West Rock Ridge State Park provides opportunities for hiking and enjoying the great outdoors, further enhancing the area's appeal for families.
Are there pet-friendly house rentals in Woodbridge?
In Woodbridge, Connecticut, there are several pet-friendly house rentals available, making it a great choice for travellers with furry companions. Many of these properties feature amenities such as spacious backyards, modern kitchens, and comfortable living areas, great for families or groups.The neighbourhood offers a serene suburban atmosphere, with easy access to local parks where pets can enjoy walks and playtime. Nearby, the beautiful West Rock Ridge State Park provides further opportunities for outdoor activities, including hiking trails that are often dog-friendly.
Are there any remote work holiday rentals in Woodbridge?
In Woodbridge, Connecticut, there are several holiday rentals suitable for remote work. Visitors can expect properties that cater specifically to working travellers, offering amenities such as complimentary Wi-Fi, dedicated desk spaces, and comfortable chairs, ensuring a productive environment. Many of these rentals also provide serene surroundings, which can be a refreshing change from a traditional office setting.The area is characterised by its picturesque suburban charm, with easy access to parks and walking trails, superb for taking breaks during the workday. Additionally, the local community offers various cafés and shops where remote workers can unwind or grab a quick bite. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Woodbridge?
In Woodbridge, popular rental amenities include features that cater to both comfort and convenience. Many holiday rentals come equipped with desks, making them suitable for those who may need to work during their stay. Air conditioning is commonly available, ensuring a pleasant environment, especially during warmer months. Travellers can also expect coffee and tea makers in most rentals, allowing for a cosy start to the day. Additionally, many properties offer decks or patios where guests can relax outdoors, as well as dining areas for enjoying meals together.
When is the best time to visit Woodbridge for a holiday rental?
April marks the beginning of the peak season in Woodbridge, making it an ideal time for those looking to book a holiday rental. The months from April to June attract visitors eager to enjoy the beautiful spring weather and engage in various outdoor activities, from hiking to local festivals. With temperatures typically ranging from 5 to 20 degrees Celsius, the climate is pleasantly mild, great for exploring the area's charming parks and nature trails.April, in particular, is a vibrant month where you can witness the blossoming of flowers and enjoy the awakening of nature. This season also brings a lively option as tourists flock to the region to participate in spring events and discover the local culture. The picturesque scenery of Woodbridge enhances any outdoor adventure, making it a great time for sightseeing and leisurely strolls through the town.If you're considering a more budget-friendly option, December can be a wonderful time to experience Woodbridge without the crowds. It's cooler, with temperatures often dropping to around 0 degrees Celsius, the town's winter charm and holiday decorations create a unique, tranquil atmosphere for those seeking a peaceful retreat.
What are the top attractions in Woodbridge?
In Woodbridge, visitors can enjoy a blend of natural beauty and cultural attractions. The charming town is home to the picturesque Lake Eloa, where outdoor enthusiasts can partake in activities such as hiking and birdwatching. Nearby, the scenic Woodbridge Green offers a peaceful setting with walking trails and picnic areas.For those interested in history, the Woodbridge Town Library is housed in a historic building and often features local events and exhibitions. The Amity Regional High School, with its impressive architecture, is another top landmark.
Are all fees included in the Woodbridge 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 Woodbridge holiday homes with parking?
Stayz offers a wide selection of holiday homes in Woodbridge 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 Woodbridge holiday homes?
You can find great discounts on holiday homes in Woodbridge 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 Woodbridge holiday home booking on Stayz?
To find Woodbridge 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 Woodbridge?
A long-stay holiday home in Woodbridge 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 Woodbridge holiday home?
Book your Woodbridge 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 Woodbridge?
Prices for holiday homes in Woodbridge 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 Woodbridge 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.