
House vacation rentals in Woodbridge
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Top-rated house rentals in Woodbridge
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Woodbridge house rentals
House rentals with a pool

2 homes in one (in-law design) w/salt water pool
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!

Spacious and relaxing New Milford 5br home w pool!
Jarret was extremely helpful and friendly. The house was exactly what we needed. I will definitely come back and stay here next time I’m in town.

Pool House
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

Garden Level Suite with Beautiful Pool
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!

Hot Tub and pool Home away from home
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!

Modern Beach Area Vacation Home With Pool
We were all very happy with the check-in/check-out. Instructions were clear and host left helpful information. Beds were quite comfortable. More than enough space for all. Laundry room was a plus. Easy to access town & beach. Lovely place - quiet - clean. Would definitely book again.

Huge Family House w/Waterviews
We had a wonderful stay! The house can accommodate large family gatherings - there were a lot of spaces for folks to spread out as well as gather. The kitchen is very well stocked. We would definitely rent again!

Newly-Renovated, Private, 4BR Cape w/Pool
Great home and host. Responsive to inquiries. Would recommend!
Weekly house rentals

Bright 3-bedroom house with ample parking & patio!
My friends and I had a wonderful time at Alyson & Costa's Fairfield house! It's an absolutely adorable space in a great area. The hosts are responsive, helpful, and kind. I would recommend this Airbnb to anyone looking to stay in this area!

1 Bdrm Apt in West Haven
I love staying here and trying to stay here. Every chance I get. Donna is truly a great person and I enjoy my stay every time. She truly makes me feel like Family and makes me feel like there’s a home away from home. I can’t wait till my next stay.

Spacious Modern Beach House
We were gathered from around the country for my Mother s Memorial. It was such a pleasure to stay in such a peaceful environment, as emotions were high. It was healing. Beautiful home, and all directions were clear. If it had been a little later in the Spring and the weather warmer, it would have been even better. I highly encourage anyone to stay and enjoy what the area has to offer in Gregory's beautiful home. You will have a wonderful vacation!

Lake Candlewood Retreat
Nice place .. host is very responsive and helpful and place is nice .. beautiful lake views .. spent 30 days while renovating my house Nd was a smooth stay..

Southport Shoreline Charm: Elegant Coastal Escape
Our stay was absolutely wonderful from start to finish! The accommodations were clean, comfortable, and well-maintained, with thoughtful touches that made us feel right at home.

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking
John and Crystal were super hosts. They communicated thoroughly and responded quickly, were flexible, and above all made us feel right at home. The location is close to everything and very quiet. The accommodations were extremely comfortable, and even though there wasn't a full kitchen, the items they provided were more than enough for our stay. The off street parking was optimal and when it did snow during our visit someone was there first thing to shovel. We appreciated the flexibility of the hosts and extended our stay. John and Crystal made our travels super easy and stress free that I know we will request to stay again! Thank you!!

The Tide Inn - Milford Home by the Beach
Great location. Love the historical background of the house. Plenty of space and well appointed. Patrick was great to work with. Everything was smooth from start to finish.

Entire House on Scenic Estate with Private Pond
We had a lovely stay. JP was extremely responsive and accommodating. The house was exactly as stated in the listing. We would stay there again if in the area.
Private house rentals

Connecticut Waterfront Home, With Hot Tub, Cozy
This was our second stay at the Riverside Blues House and once again Liza did not disappoint! This is a great location, great view and the home is pristine and beautifully decorated. My son lives nearby and when we have a large group visiting the Riverside Blues House is our home away from home. Can't wait to stay there in the warm weather and take advantage of the Ferry!! Thanks Liza!

Pet Friendly Relaxing Retreat
Really loved this airbnb! Would stay again! I love the lay out gives everyone a ton of space and was super clean. Easy 15 minute drive to most places we visited in New Haven. The only things that weren’t an issue for us but to keep in mind was the one bathroom for large groups, that can be challenging. Also, the ceilings are on the lower end for anyone over 6ft, my boyfriend had to watch his head at the doorways. Under 6 you are all good though. Lastly, one of the bedrooms has a bedroom behind it. This was not an issue at all for his but just to note. We did love that the entrance way has doors that you can close, so we actually used that as a sleeping space to have everyone more separated. We were a group of 7 and had a ton of room. All bedrooms are a pretty good size as well.

The Lakeside Nook
A perfect place for our family trip. Nestled in a peaceful beautiful area, close to the pond/lake. The home was so cozy and Monika was so responsive to our messages. Definitely would stay there again

Stylish Modern Home, 4-Bedroom, Madison CT
Sascha was a terrific host and we had a wonderful stay at his home. The home was beautiful: plenty of space to spread out, relax, and everything was incredibly clean and tidy. It was also well-stocked with everything you could need. We appreciated Sascha's friendly demeanor, and he was a pleasure to communicate with. We hope to return here in the near future for another stay.

Beach House steps from sand & Amazing Views
Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.

New England Charm!
The house had everything I needed for a business-related stay near Waterbury.

Log House, sits on 3acres. A retired mini farm.
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)

Idyllic retreat on the water <1.5 hrs to NYC.
Jonathan’s home was a great find - such a beautiful spot on the river. Everything about the home and property was as described and Jonathan was a friendly and communicative host. I would definitely book again!
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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- Yale University
- Ocean Beach Park
- Dunewood
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Rye Town Beach
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Bethpage State Park
- Marvin Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Rockland Lake State Park
- Long Island Aquarium
- Attawan Beach
- Mohawk Mountain Ski Area
- Bushnell Park
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