Holiday houses in Woodbury

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Popular amenities for Woodbury holiday rentals

Stay near Woodbury's top sights

Quassy Amusement Park & Waterpark38 locals recommend
Market Place Kitchen and Bar30 locals recommend
New Morning Market29 locals recommend
Good News Restaurant and Bar22 locals recommend
John's Cafe16 locals recommend
Flanders Nature Center13 locals recommend

Other great holiday rentals in Woodbury

Guest favourite
Home in Brewster
5 out of 5 average rating, 36 reviews

Lakefront Home 5 Bedrms, 3 Baths

PollyRating, 5 stars1 month ago
Had an incredible stay at Michael's beautiful lake house. We stayed over New Years with two other families - with a combined six young children between us - and the house could not have been more perfect for our group. The multiple common areas meant that our kids could hang in one space - watch a movie, play ping pong, pool - while the adults relaxed peacefully in another. The dining spaces easily accommodated our whole party, the kitchen was extremely well-equipped, and the lake views from the living rooms and deck were unmatched! The house is warm and beautiful, and each room is welcoming and immaculate. We also found plenty to do in Brewster and North Salem, from hiking, to a farm visit, to ice skating at the nearby ice arena. Finally, Michael was an extremely friendly, detail-oriented, accommodating, and responsive host, and we felt so welcome throughout our stay! Can't wait to return!
Guest favourite
Home in Granby
5 out of 5 average rating, 6 reviews

Lake house retreat Granby CT

ChristeRating, 5 stars2 months ago
WENT FOR A FAMILY CELEBRATION FOR THANKSGIVING WEEKEND. THE HOUSE WAS INCREDIBLY STUNNING, GREAT ENTERTAINMENT AREAS, PLENTY OF SEATING, BEAUTIFUL KITCHEN. EVEN THOUGH IT WAS THE END OF NOVEMBER, WE STILL WERE ABLE TO USE ALL THE OUTSIDE AMENITIES, THE OUTDOOR BAR, SEATING AREA, FIRE PIT, THE HEAT LAMPS WERE PERFECT & UNEXPECTED. THE OUTDOOR AREA WAS AS AMAZING AS INSIDE. THE HOUSE WAS BETTER THAN WE EXPECTED, WOULD HAVE TO SAY PERFECTION! CANNOT WAIT TO GO STAY AGAIN. THANK YOU TO NATHANIA, YOU'RE COMMUNICATION WITH US WAS QUICK & GREATLY APPRECIATED! LOVED EVERY MINUTE!
Guest favourite
Home in Millerton
4.96 out of 5 average rating, 169 reviews

Vacation Home In Millerton

TaraRating, 5 stars3 weeks ago
Nice home. Comfortable and had everything we needed. We would stay again.
Guest favourite
Cabin in Cornwall
5 out of 5 average rating, 44 reviews

Beautiful Cabin in Cornwall CT.

TaraRating, 5 stars1 week ago
Beautiful home, comfortable furniture and beds! The kitchen was well stocked with appliances, dishes, pots/pans and utensils. Books and games for all ages. I hope to stay again in the future to be able to explore and enjoy the yard and gardens :)
Guest favourite
Home in New Fairfield
4.95 out of 5 average rating, 77 reviews

The Lakeside Nook

MirandaRating, 5 stars1 month ago
Very nice house with lots of room to spread out. The tv room was our favorite. Clean bathrooms and comfortable beds. The location is not far from grocery store, hiking and wineries. It snowed the night before we left and we were nervous about going down the steep road but the neighborhood does a great job plowing. We really enjoyed our stay!
Guest favourite
Home in West Haven
4.94 out of 5 average rating, 18 reviews

Beach House steps from sand & Amazing Views

KenRating, 5 stars5 months ago
Our stay in West Haven, CT, was absolutely wonderful. The Airbnb was immaculate, well-furnished, and perfectly situated near a lovely beach. The cozy ambiance and thoughtful amenities, like fresh linens and a fully equipped kitchen, made us feel right at home. The outdoor space was a lovely bonus, providing a peaceful spot to relax and enjoy the beautiful surroundings. The close proximity to the beach was a highlight of our trip, allowing us to enjoy morning walks and sunset views with ease. The location also offered convenient access to local attractions and dining options, making our stay even more enjoyable. We highly recommend this Airbnb to anyone visiting West Haven for a relaxing and memorable getaway. Adam was a tremendous host!! We will be back for sure!
Guest favourite
Home in Bethlehem
5 out of 5 average rating, 41 reviews

Lakeview Expanse

TracyRating, 5 stars6 days ago
We had a long weekend here with two couples and our young babies looking for a peaceful and relaxing time. It did not disappoint. We throughout enjoyed cozying up by the fire and cooking meals in the huge kitchen. Kartik’s home is beautiful and very well maintained. You can tell he cares about the property and making sure his guests have the best stay possible. He was extremely responsive and made our trip that much more comfortable. We will definitely stay again and take advantage of the pool in the summer! Highly recommend this house.
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars1 month 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!

Quick stats about holiday rentals in Woodbury

  • Total rentals

    30 properties

  • Total number of reviews

    840 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 properties include access to Wi-Fi

Destinations to explore