Located around an hour’s drive north of Manhattan, the lovely town of Woodbury consists of two hamlets called Central Valley and Highland Mills. Woodbury has a colourful history, which is well-documented by the town’s historical society. The society organises talks, walks and exhibitions that delve into unique aspects of Woodbury’s rich heritage. Look out for the sandwich sign at the corner of Route 32 and Weygant Hill Road in Highland Mills to visit them on Tuesdays, Thursdays and Saturdays. Next to the society is Falkirk Estate & Country Club. You can book a tour that will allow you to experience this legendary and scenic golf club and wedding venue. If all this sounds enchanting, you’ll want to book a place to stay here to explore more of what Woodbury offers. For great options, check out this list of the top Airbnb vacation rentals in Woodbury, New York.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Malkita’s Mountainview Villa (from USD 721)
This rental is located in the hamlet of Highland Mills, which is situated at the base of the iconic Schunemunk Mountain. It offers panoramic views from the living room and has a creek at the back of the property. You can enjoy lovely views of the mountains from all the bedrooms, which are each designed according to a unique theme. The master bathroom has its own sauna and tub, perfect for relaxing in after a long day.
For entertainment, there’s a home cinema room and game room to keep young and old occupied all day.
Top guest reviews
Amenities & Room:
otherwise the house was decorated nicely and all furniture and beds are newthe view from the kitchen and dining area is stunningbeds were comfortable every room had extra pillows in the closets and tissue at the nightstandsbasement is huge has a room with bunk beds & space for gamesthe kitchen could have been better stockedCleanliness:
the rooms were all super super clean and spaciousthe house is spacious and clean and well suited for groupsthe kitchen pipe was frozen having to clean dishes in the utility sink off of the kitchenHost:
malka was very responsive with our requests and questionsmalka was a great host and we recommend staying heremalka was very responsive easy to communicate with and provided helpful recommendationsmalka was a great host the property and home was beautiful and perfect for our family of 10malka was super responsive and always available to answer any questions within 20minsRead more reviewsLocation:
we really appreciated the location which was close to the outlets we would definitely returnsuch a gorgeous home in a stunning location overlooking the mountainsthere’s a beautiful creek if you walk just a few hundred feet backwe would definitely book this place againwe had a great stay at malka's place- it was just as described and a great location
2. Great apartment with free parking (from USD 113)
Besides the laundry room, which is a shared space, you’ll have the rest of this apartment completely to yourself. You can park your vehicle for free here in the space at the rear of the building. Pets are welcome here, too. The entrance is private and you’ll get a living room along with the bedroom. The kitchen and bathroom were recently renovated.
High-speed Wi-Fi is available, which will be useful to watch shows on the Smart TV or catch up on work in the dedicated work area.
Top guest reviews
Amenities & Room:
it is exactly as it is pictured; a no-frills comfortable place for 2-3 guestsvery comfortable quiet and private spacewe enjoyed a big kitchen space and our son enjoyed netflix on tvnicely furnished and updated apartmentnice to meet u glad to stay your apartmentCleanliness:
ellie’s place was great very clean and smelled goodnice place spacious very clean and securereally clean place spacious elise was very responsivevery comfortable convenient and cleanoverall the apartment was very clean and in a quiet locationHost:
she is very responsiveellie was responsive to my questionsellie provided super clear check in details and is super responsiveellie was super responsive and helpfulRead more reviewsLocation:
the location is great- close to a delicious diner pretty quietsuper close to the outlets and a half hour drive from the metro northgreat location to hiking and other attractionsgood location easy to get around townthis place is also in a great location
Nearby Airbnb vacation rentals
3. Perfect cottage for families, Monroe
You can have a picnic or a barbecue in the great outdoors as this cottage is equipped with a gas grill and fire pit. The sleeping options here comprise two single beds in one bedroom, a full-size bed in the other bedroom and a sofa bed in the living room. If there are children in your group, you can request items, such as games, books or a high chair for their use.
You can go for walks on the nearby dirt roads or relax in the lovely yard that comes with this cottage.
Monroe, New York, United StatesSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
the cottage is super cute and comfortablethe area was beautiful and the beds were comfyher cozy cabin had everything we needed for a lovely stay for three adultsCleanliness:
the house is clean and well equippedthe place was clean and felt right at home from arrivaldeborah's space is very clean and is a perfect little space for a weekend getawaythe cabin is cozy clean comfortable and fully equippedthis property is great for get away deborah goes to great measures to make a clean homey retreatHost:
deborah was an excellent hostgreat thank you for the kind hospitality and wonderful placelovely hosts and a beautiful placeshe was very helpful with driving and check-in directionseasy check-in and helpful hostRead more reviewsLocation:
great location next to fantastic hikinglocation is quiet and peacefuldefinitely a cool location tucked awayso many state parks near by for free hikes tooperfect location for hiking and museums and wineries in monroe
4. Wonderful house with lots of space, Monroe (from USD 205)
The spacious area outside this house has been put to good use. There’s a garden that’s large enough to use for playing sports and there’s also space to park a couple of vehicles. Checking in is easy as you can do it yourself using the keys in the lockbox. Inside, you’ll find an open-plan kitchen and a dining area. The kitchen is well-equipped and has a breakfast bar.
The gorgeous seating area has a fireplace, but you’ll have to get the wood for it yourself.
Top guest reviews
Amenities & Room:
beautiful home spacious and airy layout comfortable with lots of amenitiesthe beds were incredibly comfortable we really did get to relax and recoupthe rooms were spacious and everything was included for our comfortthe house was exactly as pictured except even more comfortableCleanliness:
the place is very clean and beautifulthe house was super clean and cozy and great areathe first thing we noticed was how clean the house felt which is super importantnice clean and felt right at homevery clean pretty home inside and the property is simply gorgeousHost:
ricky was a good hostricky is a super nice hostgreat stay host was super friendly quick and responsivebeautiful property with friendly and attentive host highly recommendricky is a super cool hostRead more reviewsLocation:
great location quiet and privateit is great location on the mountains with fresh and clean airwe definitely recommend to stay at ricky's placewe had a fantastic stay at ricky's place
5. Lovely loft with verdant views, Mountainville (from USD 139)
This rental is a lovely loft that’s set atop a garage. It has high ceilings and offers wonderful views of the surrounding mountains and valleys. You’ll have complete access to the loft as well as other areas outside it, such as the backyard, side gardens and the rear deck. You’ll also be able to park your vehicle for free here. Moreover, outside are seats and a fireplace. Inside, you’ll find a kitchenette, bedroom and bathroom.
A washer and dryer are also available.
Top guest reviews
Amenities & Room:
the bed is comfortable and the ac works greatthat said the space is tastefully designed and the grounds are private and comfortablethe loft space was cozy warm and very invitingthe bed is comfortable the kitchen has a functional hot plate and is well stockedCleanliness:
super cozy quiet and cleanmost importantly everything was spankling cleantrevor’s place was a great getaway it was very clean and easy to get tothis place is beautiful it's clean and the space is so wonderful and peacefulthis place is so lovely the apartment was spotless cozy and privateHost:
lovely and responsive hosts on a picturesque propertythe hosts were extremely kind and helpfullorelei had introduced herself and assured us that both hosts are available and are super helpfulhosts were extremely generous and went above and beyond to make sure that i had a good timetrevor is a great host i couldn't say enough about how lovely this space isRead more reviewsLocation:
great location for a weekend getawayi know the location is great for hiking close to the train to take you to the citythere are many attractions and food places nearbytrevor and loreli are super hosts - and the location is outstandingif you are from the city and need to getaway this is the perfect place for you
6. Comfortable rental in the midst of nature, Cornwall (from USD 509)
Enjoy the best of nature at this rental. It’s located in a wooded area and has a creek in the backyard of this property. There’s a huge back deck, which offers a hammock, where you can unwind. You can also have a barbecue here as there’s a gas grill with a side burner, Adirondack chairs and a fire pit. Inside is a collection of unique furniture that’s made by hand from wood.
The kitchen is well-equipped with modern luxuries, such as a 14-cup Cuisinart coffee maker and other premium cookware.
Top guest reviews
Amenities & Room:
and extremely well stocked with all the necessary amenities in the bathrooms and kitchenthe kitchen and atrium dining area are awesome as well as the deck outsidethe beds were super comfortable and the kitchen was well stockedunique and comfortable exactly as described and shown in pictures will definitely returnCleanliness:
everything was very clean and comfortablethe place was spotless and so well decoratedthe house was lovely clean and had everything we neededHost:
they were great and were very responsiveleah was an amazing communicator and wonderful hostleah was such an amazing hostthe hosts leah and matthew were greatthe host is very friendly and helpful all the timeRead more reviewsLocation:
fantastic location cozy spot in the woodsthe location was perfect for a quick getaway from nycclose to excellent art attractions like storm king and dia:beaconleah's place was perfect for a mother's day weekend reunion with my adult sonsplace is very cool good location to visit hudson valleys cool towns or nature exploration
7. Excellent property with pool, Harriman (from USD 614)
If you really want to book this rental but see that the dates are blocked off, don’t worry. Just send the host a message and they may be able to unblock the dates for you. This property is located on a private road and has a spacious driveway, where up to five cars can be parked.
There are two levels to this rental. The main floor is where the master bedroom, living room, kitchen, dining area and laundry room are located. The upper floor, meanwhile, has an office area and two bedrooms.
Top guest reviews
Amenities & Room:
the kitchen was well stocked and the welcome bottles of wine/cider was a nice touchthe backyard - deck pool hot tub and fire pit were amazinggreat pool and outdoor spacewe got to enjoy the pool while having a bbq and playing family gamesthe nice size bedrooms were comfy and we really like lounging in the family roomCleanliness:
nice house that was clean and well stockedhouse was clean communication was excellent and check-in was a breezethe house was very clean and spacious for our groupthe pool and hot tub were clean and perfect for a group of our sizeeverything was clean so many amenitiesHost:
chelsea was a great host she was very responsive and accommodatingthe host is phenomenal and extremely responsive to any needs or questionschelsea was responsive and descriptivechelsea is also very responsive and kind; 10/10 recommend bookingchelsea was a lovely extremely communicative hostRead more reviewsLocation:
the short walk to a fantastic deli and the heritage trail was an awesome pluseverything was great beautiful home and locationwe had a wonderful weekend at chelsea’s place it is in a great locationsuch nice place and a great pool
8. Amazing house for a relaxing stay, Chester
Indulge in a forest retreat by booking this rental. The spacious interior is well-fitted out with everything you need for a comfortable stay. It comes complete with bedrooms, bathrooms, living areas and two kitchens. But it’s the outside that’s the highlight! There is a pool with a bar where you can swim laps or get a sun tan. A wooded area nearby invites you to explore it and there’s ample space to play some sports.
The house is secluded as it’s set back from the road and is hidden by tall trees.
Chester, New York, United StatesAccommodates: 10
Top guest reviews
Amenities & Room:
amazing house clean air conditioner is very good spacious definitely recommend 10/10the kids enjoyed the pool and the gas grill is ready to use with grilling tools/accessories providedCleanliness:
home was clean but outside needed attention like cutting grass cleaning leaves and websgreat stay and great property great communication and the house was super cleanthe pool -- a high point -- was a great size and clean as wellthe house was comfortable very clean and beautifully decorated and also very privatethe space is clean and made me feel at homeHost:
ricky was a wonderful hostthe host was incredibly friendly and attentivehe was a great hostgreat private place and fast response times from the hostricky was very responsiveRead more reviewsLocation:
the location is idealbeautiful home great location thanks rickybeautiful sprawling home close to nycthis location was perfect for usgreat place and very quietly located away from the streets of any noise
9. Home away from home for big groups, Monroe (from USD 423)
You’ll have access to everything that this rental offers for the duration of your stay. That’s a lot as, besides the house itself, there is also a yard, driveway, patio, deck, pool, sauna and gazebo — just to name a few! The pool, however, is only available from May 15 to September 1, with maintenance scheduled on Wednesdays and Sundays. Checking in is convenient as you can do it yourself by punching in the code into the keypad.
You’ll have tons of space to enjoy here and you can even bring your boat, trailer or recreational vehicle along as you can park it in the driveway.
Top guest reviews
Amenities & Room:
the rooms had a lot of natural lightlots of space and nice small poolexcellent airbnb with lots of roomCleanliness:
everything was clean and cozythe house was clean and spaciousthe house was clean and beds were comfortablegreat location great communication lots of space clean housevery clean with a large pool and many beds for my large familyHost:
ricky was a great hostricky was also such a great hostrickey is a super great hostricky was a great host very communicative and accommodatingricky was an awesome host and was very accommodating for early checkin and late checkoutRead more reviewsLocation:
ricky's place was perfect for a summer getawaythe place is about 25 min drive from this house in case interestedricky's place was beautiful and matched perfectly with the descriptions and pictureswe were a party of 8 and booked this place for our legoland tripwould highly recommend it if you're looking for a place to stay in this area
10. Party-friendly rental with fantastic amenities, Mountainville (from USD 2250)
You’ll have 6 ac (2.43 ha) and 4,300 sq ft (399.48 sq m) to luxuriate in when you book this rental. It’s designed for guests to have fun and celebrate a momentous occasion, with equipment such as party lighting, a 4K TV, games, a heated pool, a 2,500 sq ft (232.26 sq m) deck, a game court and a hot tub.
Have an outdoor barbecue using the provided grills. Other amenities include an outdoor fireplace and two fire pits.
Top guest reviews
Amenities & Room:
the view from the rooms were beautiful and breathtakingso much room an amazing pool and great viewsfrom the basketball courts to the amazing poolthe living room was also a wonderful place for all of us to congregatethe heated pool is huge and the house is so unique there is lots to see and exploreCleanliness:
we had a great time there everything was very clean and communication was easythe house was very clean and had lots of space for our groupRead more reviewsHost:
great hosts very responsivekj & emily were great hostskj was an amazing and communicative host who kindly opened his family's home to uskj and emily were amazing hosts and their home was fantastickj and emily were wonderful hosts
Delve into history at Woodbury
The historical town of Woodbury has much to offer. You will never run out of things to do here. And where to stay is not a problem, too! Just choose from our list of the best Airbnbs in Woodbury, New York, and have the best time of your life here.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to