House holiday rentals in Woodbury

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Popular amenities for Woodbury house rentals

House rentals with a pool

Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Superhost
Home in Wolcott
5 out of 5 average rating, 5 reviews

Amazing Oasis Private Pool, BBQ, Pool Table.

AmandaRating, 5 stars5 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! 😊
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 Litchfield
4.67 out of 5 average rating, 24 reviews

Litchfield Modern Farmhouse

RafaelaRating, 5 stars2 weeks ago
The house is exactly what we needed and very well located. Near restaurants, in a beautiful neighborhood and privacy. It was clean, with a big pool, a lot of space outside and with all amenities that was described. I liked so much because the house is very illuminated . I want to stay in it again .
Top Guest favourite
Home in Roxbury
5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars4 months ago
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.
Top Guest favourite
Home in Kent
4.96 out of 5 average rating, 28 reviews

Country retreat on 4 private acres

LloydRating, 5 stars1 week ago
My family and I had such a wonderful time. The home and the surroundings were so beautiful, peaceful, quiet, and relaxing. Everything was very clean, and the bed and pillows were so comfortable. My toddler especially enjoyed the cute bathtub in the master bedroom. The pool was beautiful, just wished we were there when the weather was nicer, as the water was quite cold. The restaurants nearby (10 mins away) were so good, we especially loved everything from a place called Kingsley Tavern. Overall, loved our stay and would definitely stay here again!
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
Top Guest favourite
Home in Pound Ridge
5 out of 5 average rating, 164 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MeredithRating, 5 stars2 days ago
Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!

Weekly house rentals

Guest favourite
Home in New Milford
4.91 out of 5 average rating, 93 reviews

The Getaway: Beautiful Waterfront - New Milford CT

RosemarieRating, 5 stars3 weeks ago
Enjoyed our stay in the woods with a beautiful view of the river. Easy to get to and very close to the charming town of New Milford and many good restaurants. Although right off a busy road it was quiet inside the house. The great room, which is on the top floor, is wonderful and perfect for both working and entertaining and has a full bath. It looks like the photos with an amazing view. The bedrooms and another bath are underneath. The master bedroom is the best. Just be aware you can hear the footsteps from above and not all of the bedroom windows have bug screens. The entertainment room on the lower level which opens into the yard is filled with games and a large tv and was lots of fun. The weather was cool & rainy so we didn’t use the outdoor space as much as we thought we would but there was a kayak. The house was private and although there is no interior deadbolt we felt safe. The house was clean with good heat/ac and wi fi. Hosts were responsive.
Top Guest favourite
Home in Plymouth
4.98 out of 5 average rating, 44 reviews

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

WilRating, 5 stars2 days ago
Shawn created a special place here. Love all the details, especially the skateboards and music room. The hot tub was lovely after a long day of driving, I soaked again in the morning. ColecoVision console in the game room was so nostalgic along with a great selection of other games. I really enjoyed the grounds. Even wandered down to the dam/waterfall. My mother in law, son and wife all had their own space to stretch out. I could easily spend more time here, it is not just a place to lay your head for the night.
Guest favourite
Home in Roxbury
4.9 out of 5 average rating, 50 reviews

Artist's Retreat In The Woods | Five-Acre Backyard

JulianneRating, 5 stars5 days ago
What a fabulous home! My family had a peaceful and enjoyable stay at this hidden gem! The home is spotless and has everything you need to feel at home, sleep well and cook! Thank you to a superb host!!
Superhost
Home in Newtown
4.86 out of 5 average rating, 7 reviews

Serenity by Lakefront Cottage!

LuisRating, 5 stars3 weeks ago
Definitely recommend will be there another time thanks
Guest favourite
Home in Bridgewater
5 out of 5 average rating, 32 reviews

The Art House: 5-Acre Getaway w/ AC & Firepit

BaileyRating, 5 stars6 days ago
My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!
Top Guest favourite
Home in Sharon
5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

ScottRating, 5 stars5 months ago
Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!
Top Guest favourite
Home in Morris
4.98 out of 5 average rating, 48 reviews

UB’s Corner

CatherineRating, 5 stars1 month ago
Our stay at Ellen’s Lake House was perfect. It was comfortable, clean and the view of the lake is amazing. My husband enjoyed fishing and we both loved being on the water. Ellen was helpful and made our stay a wonderful experience.
Superhost
Home in Watertown
4.92 out of 5 average rating, 24 reviews

Historic Litchfield County Home

CarterRating, 5 stars1 month ago
Yverose was wonderful. We couldn't have asked for a better spot to host our weekend get together. The house was beautiful and so comfortable - perfect for 6 girlfriends. We would love to be back one day!!

Private house rentals

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

Adorable Beach House on LI Sound

LisaRating, 5 stars1 day ago
There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!
Top Guest favourite
Home in New Milford
4.97 out of 5 average rating, 31 reviews

OWL's PERCH Candlewood Lakefront Rustic Cottage!

JackieRating, 5 stars1 week ago
If you're looking for a cute little cottage in the woods near the lake to recharge and relax - this is it! KC provided an extensive list of instructions and to know's, which made check in/check out and all the in-between fool proof. KC was super friendly and responsive as well!
Guest favourite
Home in Southbury
4.91 out of 5 average rating, 22 reviews

Cozy Family and Pet friendly 3 br Home

MichaelRating, 5 stars2 weeks ago
Ryan’s house was a perfect fit for us was very clean great location and nice and private. Any questions we had Ryan was quick to respond and even came and mowed the lawn for us. Thank you Ryan for completing our stay. We really appreciate it will definitely stay again.
Top Guest favourite
Home in Danbury
4.98 out of 5 average rating, 96 reviews

Lakeview Estate - Chef's Kitchen - NYC Getaway

AizelRating, 5 stars2 months 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 Hartford
4.96 out of 5 average rating, 69 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

EmilyRating, 5 stars3 weeks ago
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.
Top Guest favourite
Home in Newtown
5 out of 5 average rating, 16 reviews

A nestled retreat on 15 acres

SusanRating, 5 stars1 week ago
We loved this house, it's beautiful inside and out. We watched deer in the early morning and had a dozen or more flowering trees dotting our view. The house is immaculate, and the kitchen is a dream for prepping and cooking. We were able to visit Yale, ocean beaches, wonderful restaurants, and ran into two farmers markets full with welcoming artists.. we had a rainy evening and enjoyed listening to the rain while we read. It's a great location if you want to do a Gilmore Girls weekend. If you know, you know. Thank you Kathleen for sharing your home.
Guest favourite
Home in New Fairfield
4.97 out of 5 average rating, 75 reviews

Hilltop Retreat- Lakefront with Dock

JoeRating, 5 stars2 months ago
Our stay included spending family time in front of the fireplace watching Disney shows and with time spent enjoying meals around the cozy kitchen table. Enjoyed our stay very much and hope to go back one day
Top Guest favourite
Home in Newtown
4.99 out of 5 average rating, 96 reviews

Comfortable home away from home

AaronRating, 5 stars2 weeks ago
Terry and Jack’s place was perfect for us staying in Newtown visiting friends but we could also drive to Manhattan for day trips. House had everything you’d need and they even helped us get a crib delivered early/picked up later after we left. Super nice and responsive hosts! Will definitely stay again!

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