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Woodbridge Holiday Rentals

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Holiday Rentals in Woodbridge

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (61)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Business or Weekend escape

9.2 out of 10, Wonderful, (42)
"Very nice owner with great communication. "
The price is AU$226
includes taxes & fees
29 July - 30 July
Business or Weekend escape

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (5)
The price is AU$1,067
includes taxes & fees
11 Aug - 12 Aug
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

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

10.0 out of 10, Exceptional, (1)
"Such a cute vibey apartment and the host was so nice and easy to talk to--would love to stay here again!"
The price is AU$301
includes taxes & fees
29 July - 30 July
Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Modern House in Black Rock

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very easy stay and great location convenient to Fairfield University . Plenty of options to walk to for coffee or meals. Had everything we needed. Clean, well equipped. Great communication with owners. "
Modern House in Black Rock

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (19)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
Luxury Apartments by Hyatus at Pierpont

42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

8.6 out of 10, Excellent, (7)
"I rented this place because of the location and convenience to the many things we enjoy about Milford CT. The master bedroom is top-notch as well as the living space downstairs. We hoped to use the outdoor fire place make smores, but due to a medical emergency our trip was cut short. Regardless, we enjoyed our stay at 42 Wood Ave. Thank you, Tiffany, for supplying an awesome rental."
The price is AU$704
includes taxes & fees
31 July - 1 Aug
42 Wood Ave · 5 Minute Walk To Beach! Amazing Backyard Space!

Cozy 3 bedroom minutes from Yale and the beach

7.0 out of 10, Good, (2)
"Would recommend. It was quaint second story apartment in an older home. Nicely updated."
Cozy 3 bedroom minutes from Yale and the beach

Waterfront Dream Private Beach+Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (65)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Waterfront Dream Private Beach+Hot Tub+Stunning Views

Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

2.0 star property
10.0 out of 10, Exceptional, (1)
"I'd like to say that upon arriving the house was beautiful. There's a gorgeous backyard pond with a water spout in the middle. A nice accessible driveway and a cute little cobblestone walkway leading up to the entrance of the guest house. It was beautiful when we arrived inside. House was clean and inviting and there was also cold water and refreshments. Will 100% be booking again... I would give it a hundred stars if I could. Best experience ever."
Charming, Large Cozy 1-bedroom house in fabulous Berlin with WiFi, near Hartford

Minutes to Walnut Beach, newly renovated 3 bedroom home

10.0 out of 10, Exceptional, (6)
"Very nice place."
Minutes to Walnut Beach, newly renovated 3 bedroom home

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (51)
"Great location, great stay!"
Luxury Furnished Apartments by Hyatus Downtown at Yale

StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.

2.0 star property
10.0 out of 10, Exceptional, (9)
"The property is clean ,comfortable tastefully decorated, convenient to many locations. Host communication is great! Highly recommend!"
StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

10.0 out of 10, Exceptional, (1)
"This property is absolutely beautiful. Extremely clean. The host was very attentive to my questions before and after check in. The host checked on my family during our stay. The yard, the porches, and the entire interior are so cozy and comfortable. The check in and check out processes were smooth. The neighborhood is quiet. I am already looking forward to going back! Definitely recommend the Beechmont House"
The price is AU$2,149
includes taxes & fees
1 Aug - 2 Aug
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (16)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is AU$1,373
includes taxes & fees
29 July - 30 July
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (64)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
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

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?

Business or Weekend escape: This holiday home rental outside of Woodbridge is equipped with a BBQ, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

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.