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House holiday rentals in Woodbridge

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Popular amenities for Woodbridge house rentals

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.
Superhost
Home in New Haven
5 out of 5 average rating, 14 reviews

The Jewel of The Cove - Historic Coastal Retreat

DaraRating, 5 stars1 month ago
Edward made the stay easy and we were very comfortable. House is lovely and very very clean. Would stay at the house again!
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!

Private house rentals

Top Guest favourite
Home in Plymouth
4.98 out of 5 average rating, 42 reviews

Don’t miss out on this cozy escape! w/Skatepark

ChristopherRating, 5 stars3 days ago
Would gladly stay here again. Shawn was responsive and the place had everything we needed. Hope to come back to this part of CT again
Superhost
Home in West Haven
4.87 out of 5 average rating, 70 reviews

McAngel Haven: 5 mins from Yale

RebaRating, 5 stars1 week ago
We enjoyed our stay at this spacious and clean house. Our family had a remarkable stay. Angela was great!
Top Guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars1 month ago
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!
Top Guest favourite
Home in New Haven
5 out of 5 average rating, 67 reviews

3BD w/ Hot Tub + FRER EV | Close 2 Beach +Yale

ShebellRating, 5 stars1 week ago
Wow, I don’t even know where to start! My family and I just had the most incredible time celebrating my niece's 21st birthday. From the moment we arrived, Annie blew us away as the ultimate host! The house was decked out with beautiful decorations that truly made the surprise unforgettable. And guess what? She even had a magnificent birthday cake waiting for us! The house itself was absolutely gorgeous and so inviting. We felt right at home with an abundance of linens, towels, and toiletries—perfect for a group of five women! The jacuzzi was a dream, and the grill was all set for us to fire up some delicious meals. Plus, the kitchen was stocked with all the essentials and some delightful extras! Annie was always quick to respond to our questions, which made everything even easier. We were thrilled to find beach necessities already available, so we didn’t have to worry about bringing our own. There’s so much more I could rave about, but overall, this stay was amazing.
Top Guest favourite
Home in Milford
4.98 out of 5 average rating, 53 reviews

Luxury Beach House | 3 Bd-King | Chef Kitchen |4 TV

KristenRating, 5 stars3 days ago
Highly recommend this home! We had 5 adults and is a fantastic spot for a family vacation! Lots to do with access to cedar beach and walking trails as well as a very short ride to a local restaurants! House was spotless and owners were very responsive we had prior and during the trip, checking in to make sure we didn’t have any issues!
Superhost
Home in New Haven
4.77 out of 5 average rating, 69 reviews

Cozy apartment feel at home

BrittanyRating, 5 stars3 weeks ago
Great spot super close to everything we needed to go to. It was so cozy that we ended up sleeping through a bunch of our plans 😂 appreciate having pet friendly places like this since we like to travel with our pups. It was clean and quiet for being attached to another residence.
Top Guest favourite
Home in Woodmont
4.99 out of 5 average rating, 95 reviews

2 Bedroom with sweeping views of Long Island Sound

NikkiRating, 5 stars2 weeks ago
Stayed here with another couple over the weekend for a wedding - this place was perfectly suited for us! Just wish the weather had been better so that we could’ve enjoyed the deck more as it is overlooking the sound! We were all saying, as we checked out this morning, that if we end up in town again, we would absolutely stay here if it were available!
Top Guest favourite
Home in Watertown
4.96 out of 5 average rating, 26 reviews

Carriage House on Smith Pond!

BetsyRating, 5 stars2 days ago
By far one of the nicest air B&B’s we’ve stayed in. Beautifully renovated carriage house on an incredible piece of property. Todd and Janet warmly welcomed us with their chickens’ fresh eggs, fruit and muffins. Kitchen was well equipped for preparing meals and we enjoyed dining al fresco while hawks flew and deer ran across the fields. Upstairs is a comfortable bed with nice linens and a large bathroom. This is a real gem! We hope to return in the future.

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

  • Wi-Fi availability

    30 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore