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Woodbridge Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Woodbridge holiday rentals

A kitchen with white cabinets, a black refrigerator, a double sink, and a window overlooking a wooded area.

1. Serene Country Cottage

Serene Country Cottage
Woodbridge
8.0 out of 10, Very good, (11 reviews)
"We had a great one night stay here! The place is really cute, clean and comfortable. One of the greatest parts about the stay was the host, Trent. He was welcoming and VERY responsive to questions! "
United States
felicia
The price is NZ$382
includes taxes & fees
2 Nov - 3 Nov
Serene Country Cottage
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

2. Stylish Westville Apartment near Yale Campus

Stylish Westville Apartment near Yale Campus
West New Haven
9.0 out of 10, Wonderful, (4 reviews)
"Great location, well organized space, well decorated. I loved that there were enough places to sit and be comfortable, many VRBO’s have tiny little sofas that are so uncomfortable, but this has proper furniture. The beds are very firm."
Canada
Alex C.
The price is NZ$435
includes taxes & fees
14 Oct - 15 Oct
Stylish Westville Apartment near Yale Campus
A dining area with a long table, four chairs, a chandelier, and a painting on the wall.

3. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (80 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is NZ$367
includes taxes & fees
14 Oct - 15 Oct
Spacious 2 Bedroom apartment close to Yale Bowl
A bedroom with a bed, a blue sofa, a radiator, a window with blinds, a dreamcatcher, and a framed picture on the wall.

4. One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
9.4 out of 10, Exceptional, (3 reviews)
"The property is immaculate and the service very responsive."
United States
Stephanie G.
The price is NZ$308
includes taxes & fees
27 Oct - 28 Oct
One bedroom in United States of America, New Haven
A living room with a flat-screen TV mounted on the wall, a yellow armchair, a patterned rug, and various decorative items on shelves and side tables.

5. The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (17 reviews)
"It was the perfect day and very convenient for our trip for our son’s graduation. Thank you for being so receptive and helpful."
United States
Michele B.
The price is NZ$425
includes taxes & fees
14 Oct - 15 Oct
The Sicilian
Exterior

6. Prime Yale Studio Steps to Sallys Apizza

Prime Yale Studio Steps to Sallys Apizza
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great stay - and it is close to Sally's! We had a nice visit and all was as represented for the property."
United States
Milton W.
The price is NZ$364
includes taxes & fees
14 Oct - 15 Oct
Prime Yale Studio Steps to Sallys Apizza
A neatly made bed with a checkered blanket, white pillows, and a framed picture on the wall.

7. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, Wonderful, (15 reviews)
"We had a very nice stay here! The hosts were lovely and very communicative, and they were able to help us with any problems we had very quickly."
United States
Luke
The price is NZ$312
includes taxes & fees
2 Nov - 3 Nov
Yale Casa Verde Studio
A modern apartment with a green sofa, a wooden dining table, and a kitchen in the background.

8. Modern Westville Home near Yale and Hospitals

Modern Westville Home near Yale and Hospitals
West New Haven
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable space. Excellent location and parking was a plus. We have stayed here twice and would definitely recommend to friends or family. "
United States
Thomas B.
The price is NZ$427
includes taxes & fees
26 Oct - 27 Oct
Modern Westville Home near Yale and Hospitals
A cozy living room with a grey sofa, a coffee table with books and a vase of flowers, and bookshelves filled with books and decorative items.

9. Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very good, (9 reviews)
"We had a good time. Did some relaxing, a little beachtime and ate some good food."
United States
Erin S.
The price is NZ$449
includes taxes & fees
14 Oct - 15 Oct
Spacious Bohemian Nook
A cozy living room with a sofa, armchair, round table, and a bed with a headboard.

10. Enjoy a comfortable stay in New Haven, perfectly located near Yale and the city’s top attractions. This cozy home offers a peaceful neighborhood setting while keeping you just minutes from downtown dining, shopping, and cultural spots.

Enjoy a comfortable stay in New Haven, perfectly located near Yale and the city’s top attractions. This cozy home offers a peaceful neighborhood setting while keeping you just minutes from downtown dining, shopping, and cultural spots.
West New Haven
The price is NZ$564
includes taxes & fees
16 Oct - 17 Oct
Enjoy a comfortable stay in New Haven, perfectly located near Yale and the city’s top attractions. This cozy home offers a peaceful neighborhood setting while keeping you just minutes from downtown dining, shopping, and cultural spots.
A kitchen with white cabinets, a stove, and a dining table with chairs.

11. Yale Science Park 1BR | Free Parking

Yale Science Park 1BR | Free Parking
Dixwell
8.0 out of 10, Very good, (8 reviews)
The price is NZ$427
includes taxes & fees
14 Oct - 15 Oct
Yale Science Park 1BR | Free Parking
A row of brownstone buildings with a central staircase leading to the second floor.

12. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is NZ$428
includes taxes & fees
14 Oct - 15 Oct
Bright Downtown Studio near Yale & East Rock!
Interior

13. Château Blanc | Near Yale University

Château Blanc | Near Yale University
Dwight
8.6 out of 10, Excellent, (9 reviews)
"Perfect for a quick trip and one night stay!"
United States
Chris D.
The price is NZ$322
includes taxes & fees
2 Nov - 3 Nov
Château Blanc | Near Yale University
A spacious lobby with a large chandelier, a central round table with a vase, and a checkered floor.

14. Yale Deluxe Modern Apartment

Yale Deluxe Modern Apartment
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"Great spot close to everything with a secure entrance to the building. Easy access to the unit Quick responses and good communication from the host. Great unit with lots of amenities! Definitely would stay here again and again!!"
United States
Anonymous traveller
The price is NZ$331
includes taxes & fees
9 Nov - 10 Nov
Yale Deluxe Modern Apartment
A house with a front porch, a garage, and a well-maintained lawn.

15. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is NZ$624
includes taxes & fees
14 Oct - 15 Oct
Angelica’s safe haven @ west haven
A modern living room with a large mirror, a wooden accent wall, a grey sofa, and a large window with white curtains.

16. The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.

The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
Downtown New Haven
10.0 out of 10, Exceptional, (6 reviews)
"Great little downtown apartment! Small - good for up to two people. Nicely appointed and decorated, great sectional sofa, big TVs where we wanted them. Host was kind and helpful and accommodating. Location is pretty much across State St from the State Street RR Station, a block and a half from the Green, and near everything. Orange Street (half a block away) has a ton of bars and restaurants. We enjoyed our stay!"
United States
George Z.
The price is NZ$594
includes taxes & fees
14 Oct - 15 Oct
The Elm - Retreat Near Yale, Parking, Gym, DTWN, Wooster Sq & Union Stn.
A living room with a TV, sofa, coffee table, and a staircase leading to an upper level.

17. Modern Loft Near Yale |Wooster Sq| 5 Star Location

Modern Loft Near Yale |Wooster Sq| 5 Star Location
Downtown New Haven
10.0 out of 10, Exceptional, (1 review)
"My wife and I loved this unit. The host was the quickest to respond to questions that we have encountered. My only issue was the parking. There is a 19 charge per day to park in the parking lot. There is limited and restricted street parking. We got lucky because we were there on a weekend night."
United States
Eric P.
Modern Loft Near Yale |Wooster Sq| 5 Star Location
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a white table and chairs.

18. Stylish Wooster Square Home Walk to Yale

Stylish Wooster Square Home Walk to Yale
Downtown New Haven
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful apartment in the Wooster neighborhood. New, modern, comfortable apartment within walking distance to great restaurants. Nicely appointed with easy check-in and parking for one car. Was perfect for two couples visiting their Yale students for the weekend!"
United States
Lydia P.
The price is NZ$554
includes taxes & fees
14 Oct - 15 Oct
Stylish Wooster Square Home Walk to Yale
A living room with a sofa, coffee table, and a large mirror. There are windows, a plant, and a bookshelf.

19. A brick's throw away to Sally's Apizza!

A brick's throw away to Sally's Apizza!
Wooster Square
8.8 out of 10, Excellent, (5 reviews)
"The perfect place for visiting my Yale student! The space was comfortable for her to come visit, far enough from campus for a beak but close enough to get to class. Loved the full kitchen to provide her a home cooked meal and access to the washer and dryer so we could do her laundry. We can’t wait to stay again! I highly recommend both coffee locations and the liquor store in the neighborhood. And of course Sally’s! The host was amazing and communicated nearly immediately when I had questions! "
United States
Brandi J.
The price is NZ$571
includes taxes & fees
26 Oct - 27 Oct
A brick's throw away to Sally's Apizza!
A rooftop patio with outdoor seating, string lights, and a city skyline view.

20. Modern Elegant Stay by Yale • Gym • Rooftop Terrace

Modern Elegant Stay by Yale • Gym • Rooftop Terrace
Dwight
10.0 out of 10, Exceptional, (9 reviews)
"This was our second stay. Clean, excellent location and owner is the best! Will book again!"
United States
Kelly E.
The price is NZ$390
includes taxes & fees
8 Nov - 9 Nov
Modern Elegant Stay by Yale • Gym • Rooftop Terrace
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 Woodbridge Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

8/10 Good
"A fairly clean hotel with very nice staff! The only thing that bothered us was the constant smell of weed/marijuana every day we were there."
Denise 3-night trip
Posted 1 hour ago
Holiday Inn Express Southington by IHG

Find out more about Woodbridge

Everything you need to know about Woodbridge 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 Woodbridge 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 Woodbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodbridge. 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 Woodbridge 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 Woodbridge holiday rentals we have selected for you start as low as NZ$140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodbridge rentals

At Expedia, we put the best Woodbridge 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 Woodbridge 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 Woodbridge 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 Woodbridge. 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 Woodbridge?

Yes, there are holiday rentals close to the most popular sights in Woodbridge, or you can select a more secluded option if you're looking for a relaxing stay. Woodbridge is known for its restaurants and shopping. Make sure you have time to check out the art while you're in the area.

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

New Madison beach house - Ocean front- Great views- booking Summer 2026: This holiday home rental outside of Woodbridge is located on the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Woodbridge?

While exploring the area, visit family-friendly sights like Peabody Museum of Natural History, or get outside and enjoy nature at New Haven Green. While here, West Rock Ridge State Park and Beverly Kaye Gallery are other places worth a visit.

What are holiday rentals like in Woodbridge?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodbridge. Holiday rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for families.