Vacation rentals with a pool in Hudson

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Popular amenities for Hudson rentals with a pool

House rentals with a pool

Superhost
Home in Woodbury
4.95 out of 5 average rating, 19 reviews

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

ChristineRating, 5 stars8 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 Saugerties
4.94 out of 5 average rating, 71 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

YokoRating, 5 stars2 weeks ago
As soon as we walked into Sarah’s place, my daughter proclaimed it the “BEST HOUSE EVER!!” Everything was clean and organized, and there were so many little things that helped us feel right at home. The house is perfectly thought out for families with young kids and made our stay so convenient - from baby gates, step stools, high chairs, kids’ kitchenware, lots of toys and books, and of course - the treehouse. The house is a ~15 min drive of Saugerties, Woodstock, Tannersville, etc, which made it so convenient to get around and go out to eat. We also did hiked the Kaaterskill Falls, which was absolutely beautiful. We had a lovely, relaxing stay at Sarah’s, and my kids have been asking to go back again soon!
Guest favorite
Home in Saugerties
4.98 out of 5 average rating, 60 reviews

Upstate Family-Friendly House w/ Pool Pets Allowed

NasimRating, 5 stars5 months ago
We had a great time at Natalia house, a very big house with a lot to do for my three years old daughter. Will definitely stay here again.
Guest favorite
Home in Newburgh
4.84 out of 5 average rating, 86 reviews

Entire Home (private pool), Event Friendly

BernardRating, 5 stars1 week ago
The place is fun comfortable, private peaceful completely enjoyable. The hoste was great and response quickly.
Guest favorite
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars3 months ago
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.
Guest favorite
Home in Kingston
4.83 out of 5 average rating, 72 reviews

Beaver | Pool, Firepit, Secluded, 10 acres

IvanRating, 5 stars1 day ago
The home was stunning and incredibly cozy. Extremely spacious with many places to lounge. The pool was fantastic during our entire stay. Hava was a great host!
Superhost
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars6 months ago
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.
Guest favorite
Home in Woodstock
4.86 out of 5 average rating, 133 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

SteveRating, 5 stars1 month ago
A pretty mountain home with great views from the decks. The place was clean and well appointed.

Condo rentals with a pool

Guest favorite
Condo in Hunter
4.87 out of 5 average rating, 87 reviews

Cozy Gem with Mountain Views

AbishekRating, 5 stars1 week ago
Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.
Guest favorite
Condo in Windham
5 out of 5 average rating, 21 reviews

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

JaneRating, 5 stars6 months ago
I had an amazing stay! The home was spotlessly clean, beautifully furnished, and fully stocked with everything I needed for a comfortable stay. It was the perfect place to relax and unwind—definitely a gem!
Guest favorite
Condo in Windham
4.89 out of 5 average rating, 192 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

RandolphRating, 5 stars1 month ago
Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!
Guest favorite
Condo in Hancock
5 out of 5 average rating, 8 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

JoelmaRating, 5 stars6 months ago
Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.
Guest favorite
Condo in Hancock
4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

EladRating, 5 stars1 month ago
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.
Superhost
Condo in New Ashford
5 out of 5 average rating, 5 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

NicoleRating, 5 stars3 months ago
This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!
Superhost
Condo in Windham
4.73 out of 5 average rating, 280 reviews

Summer Retreat w/ Balcony & inground Pool

AndrewRating, 5 stars2 weeks ago
Was as advertised. Would recommend
Guest favorite
Condo in Hancock
4.92 out of 5 average rating, 65 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

MeganRating, 5 stars1 month ago
Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.

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