House vacation rentals in Woodbridge

Find and book unique houses on Airbnb

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Popular amenities for Woodbridge house rentals

House rentals with a pool

Guest favorite
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
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!!
Guest favorite
Home in New Milford
4.95 out of 5 average rating, 21 reviews

Spacious and relaxing New Milford 5br home w pool!

ElizabethRating, 5 stars4 months ago
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.
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
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.
Top guest favorite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 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 favorite
Home in Middletown
4.95 out of 5 average rating, 40 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars3 months ago
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!
Superhost
Home in Fairfield
4.71 out of 5 average rating, 7 reviews

Modern Beach Area Vacation Home With Pool

VRating, 5 stars17 months ago
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.
Guest favorite
Home in Woodmont
5 out of 5 average rating, 9 reviews

Huge Family House w/Waterviews

LynnRating, 5 stars6 months ago
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!
Superhost
Home in Fairfield
4.94 out of 5 average rating, 35 reviews

Newly-Renovated, Private, 4BR Cape w/Pool

PeterRating, 5 stars7 months ago
Great home and host. Responsive to inquiries. Would recommend!

Weekly house rentals

Superhost
Home in Fairfield
4.86 out of 5 average rating, 81 reviews

Bright 3-bedroom house with ample parking & patio!

AiméeRating, 5 stars2 months ago
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!
Top guest favorite
Home in West Haven
5 out of 5 average rating, 11 reviews

1 Bdrm Apt in West Haven

RogerRating, 5 stars3 months ago
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.
Guest favorite
Home in Branford
4.89 out of 5 average rating, 53 reviews

Spacious Modern Beach House

BeckyRating, 5 stars1 week ago
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!
Guest favorite
Home in Brookfield
4.82 out of 5 average rating, 22 reviews

Lake Candlewood Retreat

FabioRating, 5 stars5 months ago
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..
Superhost
Home in Fairfield
4.81 out of 5 average rating, 122 reviews

Southport Shoreline Charm: Elegant Coastal Escape

OctavioRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Fairfield
4.9 out of 5 average rating, 106 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

Corri AnnRating, 5 stars2 months ago
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!!
Guest favorite
Home in Milford
4.92 out of 5 average rating, 13 reviews

The Tide Inn - Milford Home by the Beach

MarkRating, 5 stars5 days ago
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.
Guest favorite
Home in Norwalk
4.89 out of 5 average rating, 37 reviews

Entire House on Scenic Estate with Private Pond

KristyRating, 5 stars1 month ago
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

Top guest favorite
Home in Rocky Hill
4.95 out of 5 average rating, 21 reviews

Connecticut Waterfront Home, With Hot Tub, Cozy

LauraRating, 5 stars3 weeks ago
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!
Superhost
Home in North Haven
4.43 out of 5 average rating, 7 reviews

Pet Friendly Relaxing Retreat

CristinaRating, 5 stars7 months ago
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.
Guest favorite
Home in New Fairfield
4.95 out of 5 average rating, 79 reviews

The Lakeside Nook

MarisaRating, 5 stars2 weeks ago
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
Top guest favorite
Home in Madison
5 out of 5 average rating, 28 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

AlanRating, 5 stars1 month ago
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.
Guest favorite
Home in West Haven
4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

DonnaRating, 5 stars1 week ago
Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.
Top guest favorite
Home in Middlebury
5 out of 5 average rating, 10 reviews

New England Charm!

DavidRating, 5 stars3 months ago
The house had everything I needed for a business-related stay near Waterbury.
Superhost
Home in Ridgefield
4.81 out of 5 average rating, 21 reviews

Log House, sits on 3acres. A retired mini farm.

TaylorRating, 5 stars2 weeks ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)
Top guest favorite
Home in New Milford
4.97 out of 5 average rating, 106 reviews

Idyllic retreat on the water <1.5 hrs to NYC.

BenjaminRating, 5 stars4 days ago
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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