House vacation rentals in Woodbridge

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Popular amenities for Woodbridge house rentals

House rentals with a pool

Guest favourite
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 favourite
Home in North Fork
4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

KimRating, 5 stars5 months ago
This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!
Top guest favourite
Home in North Fork
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars8 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Guest favourite
Home in Stony Brook
4.93 out of 5 average rating, 524 reviews

Spacious Studio Apartment- near SBU

ElvisRating, 5 stars2 weeks ago
Great place to stay. There are occasional noises upstairs but area is nice and weight. Unit was very clean as well.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars3 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
Top guest favourite
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 favourite
Home in Stamford
4.96 out of 5 average rating, 248 reviews

Midcentury Modern ZenHouse Sculptor Studio

GonzaloRating, 5 stars2 weeks ago
I stayed here for a weekend and I wished I would have stayed longer. Perfect spot for a getaway and relaxation. Olga was a really caring and warm host, super attentive at all time, always saved some food for us when she cooked. The house was clean, organized, with natural lighting everywhere surrounded by a beautiful garden and a river with ducks and a swan. I would recommend this place to anyone who’s looking to relax, have a weekend to themselves and enjoy nature.
Guest favourite
Home in North Fork
4.92 out of 5 average rating, 24 reviews

North Fork Farmhouse with Saltwater Pool

MikeRating, 5 stars5 months ago
Had a great stay at Andrew’s Air Bnb. It was very close to numerous wineries, breweries, and restaurants. It was the perfect location for a weekend get away, with a house that would’ve been worth it in the middle of nowhere! We will be back!

Weekly house rentals

Superhost
Home in Westbrook
4.85 out of 5 average rating, 195 reviews

Family-Friendly Cottage by The Shore

TristanRating, 5 stars2 weeks ago
I had a nice, overnight stay at Marie's place. All was as described and the instructions for everything were spot on. Comfortable & convenient stay, would visit again!
Top guest favourite
Home in Wading River
4.96 out of 5 average rating, 501 reviews

Your Zen Retreat

AliciaRating, 5 stars2 weeks ago
This getaway was very last minute and there was huge importance on it because I needed some time away and because I had never booked an Airbnb before. I wanted to make sure that my family and I were able to be someplace peaceful and have a really good time and Brian’s home provided just that. The stay was so much more than we expected and Brian was absolutely amazing. He’s super responsive and accommodating. Hoping to stay here again in the near future!
Guest favourite
Home in New Milford
4.99 out of 5 average rating, 84 reviews

Waterfront Family Retreat on Candlewood Lake

AshleyRating, 5 stars1 month ago
Had a great stay with my family. Home was even better than the pictures, very clean with all the amenities! Great yard to entertain and play with the kids when the weather was nice!
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 115 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars3 weeks ago
Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!
Guest favourite
Home in New Britain
4.9 out of 5 average rating, 106 reviews

5•Star CapeCodStyle Gem with a Bedroom on the Main

GregRating, 5 stars4 days ago
We had a great stay at Chana’s place. She was very easy to communicate with and the house was comfortable and very clean. We’d love to stay again next time we’re in CT!
Guest favourite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars6 months ago
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.
Guest favourite
Home in North Fork
4.95 out of 5 average rating, 103 reviews

Walk to Vineyards, Beach, Restaurants • Sleeps 8

MeredithRating, 5 stars1 month ago
Matthew was a gracious host, friendly and communicative! We enjoyed our stay in his home and in Jamesport
Guest favourite
Home in East Hampton
4.92 out of 5 average rating, 93 reviews

Clean private home near Lake Pocotopaug!

CathyRating, 5 stars4 months ago
I highly recommend this property. It was perfect for our Christmas visit with family. The furniture and beds were very comfortable. We truly enjoyed our stay in East Hampton. We will be back!

Private house rentals

Superhost
Home in North Haven
4.43 out of 5 average rating, 7 reviews

Pet Friendly Relaxing Retreat

CristinaRating, 5 stars8 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 favourite
Home in North Fork
5 out of 5 average rating, 17 reviews

Waterfront with private dock & bocce court

AlisonRating, 5 stars5 months ago
We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️
Superhost
Home in Clinton
4.91 out of 5 average rating, 11 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

HannahRating, 5 stars4 months ago
We had a group of 8 adults and 7 kids (5 and under) and the space was great for a large group! There was plenty of room for the kids to run around downstairs and the large yard was fantastic. We were there in the winter so couldn’t take advantage of the pool but we did make a trip to the local beach (5 min drive) and use the fire pit. I definitely recommend Gregory’s place for both larger groups and families! We would love to return!
Guest favourite
Home in Milford
5 out of 5 average rating, 9 reviews

Renovated House on Private Cedar Beach

PeterRating, 5 stars7 months ago
The house was perfect and what we expected for a quick couples getaway. Steps from the beach. good local restaurants. Close enough to concert venues without having to stay in Bridgeport.
Superhost
Home in North Fork
4.75 out of 5 average rating, 4 reviews

Beachfront Retreat - 5BR Home with Stunning Views

KaranRating, 5 stars1 week ago
Amazing place , impressive host, Good people. Nichole was great.
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top guest favourite
Home in Middlebury
5 out of 5 average rating, 11 reviews

New England Charm!

DavidRating, 5 stars1 week ago
I've stayed her many times for business trips. Always convenient, comfortable and quiet. Meets my needs ideally.
Superhost
Home in Ridgefield
4.81 out of 5 average rating, 21 reviews

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

TaylorRating, 5 stars3 weeks ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)

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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