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House holiday rentals in Woodbridge

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Popular amenities for house rentals in Woodbridge

House rentals with a pool

Guest favourite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars1 month ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Guest favourite
Home in Stony Brook
4.93 out of 5 average rating, 535 reviews

Spacious Studio Apartment- near SBU

ElizabethRating, 5 stars2 weeks ago
Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!
Superhost
Home in Wolcott
5 out of 5 average rating, 4 reviews

Amazing Oasis Private Pool, BBQ, Pool Table.

AmandaRating, 5 stars2 days ago
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! 😊
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars1 week ago
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.
Superhost
Home in Woodmont
4.83 out of 5 average rating, 90 reviews

Spacious 4 bedroom, oasis with ocean views galore

ChrissyRating, 5 stars3 days ago
We had a wonderful girls weekend at Allana’s house by the sea! When we had a small incident with the keypad, Allana was quick to answer my call and resolve the issue no problem. Everything was clean and beautiful! We especially enjoyed the screened in porch in the back to enjoy our meals. The view from the master bedroom and deck is incredible! We highly recommend and will be back!
Guest favourite
Home in Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend
Guest favourite
Home in Port Jefferson
4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars1 week ago
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.

Weekly house rentals

Superhost
Home in North Branford
4.9 out of 5 average rating, 10 reviews

The Gait House at High Gait Farm

NancyRating, 5 stars2 weeks ago
Lori was very accommodating to us with early check in. The beds were super comfortable, and I was so happy to see that she had two king sized beds and one queen! Perfect for our family. Beautiful linens, tons of comfy white towels in the bathrooms. Really a great place to stay that I would highly recommend.
Superhost
Home in West Haven
4.83 out of 5 average rating, 42 reviews

The Seabreeze

JulieRating, 5 stars6 months ago
Beautiful sunrise/sunset from living room. Very quiet. Joann very responsive.
Guest favourite
Home in West Haven
4.96 out of 5 average rating, 45 reviews

Westshore Luxury

MatthewRating, 5 stars1 week ago
You, was great. Traveling through and not knowing much about the area. Yu gave us so much helpful information. Be sure to ask Yu about their great restaurant in New Haven.
Guest favourite
Home in Bridgeport
4.9 out of 5 average rating, 50 reviews

Lavish retreat near downtown

LauraRating, 5 stars2 weeks ago
we love the place, Natalie was always communicative and helpful. well equipped the apartment definitely 100% recommended to anyone.
Top guest favourite
Home in Woodmont
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars1 week ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!
Superhost
Home in North Haven
4.83 out of 5 average rating, 35 reviews

Trail-side Haven Retreat! Pet friendly

KimberlyRating, 5 stars5 months ago
This property is in New Haven, bordering North Haven. Easily accessible from the 91 or from SR15, but not near enough either road to hear traffic noise. This is a downstairs unit, and there are tenants above; you will hear some neighborly noise, but nothing out of the ordinary for a duplex, and much quieter than a hotel room. If you're familiar with the area, this home is walking distance from the large Medtronic facility and a close drive to the North Haven shopping area (Target, Cinemark). Property is well kept, and all linens and interior areas were clean. We appreciated the pet-friendly approach (minimal rugs on the floor), as well as the large (unfenced) yard for our dog. We had a few minor issues, to which the hosts were quick to respond and remedy. The kitchen has every feature or appliance you'd need for a short stay, and even included common spices, soap, paper towels, and kcups. Bathroom had ample towels for 2 people. Would be happy to stay here for future visits.
Top guest favourite
Home in Milford
4.97 out of 5 average rating, 37 reviews

Modern Beach Mood!

ElizabethRating, 5 stars1 month ago
Great spot in a great location! Cole was flexible and communicative. Would love to stay again next time I’m in Milford!
Guest favourite
Home in East Hampton
5 out of 5 average rating, 19 reviews

CT River Retreat - Modern Home with CT River Views

BrianaRating, 5 stars2 weeks ago
We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!

Quick stats about house rentals in Woodbridge

  • Total rentals

    30 properties

  • Total number of reviews

    850 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

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