
Holiday rentals with a pool in Claverack
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Top-rated rentals with a pool in Claverack
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House rentals with a pool

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

NEW! Catskill Family Hideout with Seasonal Pool
What a great spacious home. Plenty of room for the whole family. Clean and neat! Beds were super comfortable! Great water pressure. Beautiful back yard and three season porch. This was our second visit here and it was just as great as the first!!

Entire Home (private pool), Event Friendly
We had a great time for my sister in law’s bachelorette. About an hour from Warwick Winery but worked our way back to the more local ones. Had a minor issue with the hottub but Faisal offered to send someone to fix it in the moment, which def was not necessary. Would absolutely stay at this house again!

Harrison Field Upstate NY Weekend Getaway
We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!

New 8BR/4B home Pool, Hottub & sauna in Hunter
We went on a family summer vacation and we had an amazing experience! The house was clean and spacious and even nicer then the pictures listed. The pool was clean the sauna worked well. There are air condions in all the rooms and David was extremely helpful. it's a beautiful area with a lots of attractions for kids and adults close by, we hope to come back again

Bright Mid-Century Modern Retreat-90 min from NYC
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.

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub
Such a great experience that reaffirms how hard hosts work! Robyn communicated the weather problems in advance and let us know things might be iffy getting in because of a winter storm. Instead of just making sure the home itself was pristine, relaxing, and totally picturesque, she made sure our arrival was perfect. Snow plowed, everything iced, bag of goodies hung up on our arrival. It was such incredible, flexible caretaking of the property and the guests! Besides that, onto the regular stuff- awesome kitchen, hot tub, bedrooms, everything super clean. Was a perfect winter stay!

Six-bedroom country house with pool and hot tub
Derek's place is great for a family get together! So many beds/bedrooms and spread out for privacy! There are so many sitting areas throughout the house and a great pool and hot tub area. The backyard is beautiful. It is so peaceful and relaxing there. The owners give you a booklet of the many places to go nearby, which is a great reference. The town of Great Barrington has a wonderful farmer's market and unique stores. So much to look at. Can't wait to go back!!
Condo rentals with a pool

Cozy Mountain hideaway Windham, Hunter
Cozy home base for a quick trip to ski at Windham! Perfect for two adults and a dog. Loved sitting on the balcony as the sun set and we enjoyed the fireplace. Super close to the Windham Path, great restaurants nearby.

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

Lovely stylish 2-bedroom condo with community pool
Had a great stay. Great location next to the mountain. Comfortable beds. Highly recommend for a ski weekend.

Condo Resort at Jiminy Peak Ski Mountain's Base
Thank you to Hamilton & Christelle for the great resort stay! Check in was easy at the main Club Wyndham Bentley Brook building. The front desk kindly provided us with a pack-n-play and sheets for our toddler. The condo was right next to the bunny slope lift and comfortably fit eight people. We also enjoyed the hot tub, pool, sauna, and gym in the main building during our stay. The slopes were decently groomed and we got lucky with a big snowstorm the last day which made for pristine night skiing! There is a washer/dryer right in the unit and a fully supplied kitchen. They provide dish soap, sponges, laundry/dish detergent packets, tissues, paper towels, and bath soaps, so no need to worry about packing extra. If you think of anything else I'm sure the front desk could help you out, and there is a small country store on the resort campus for sandwiches and basic groceries. The restaurant nearby, Bluebird, gets pretty booked, so I recommend making reservations well ahead of time.

Windham-Hunter Lodge
Cullen was an exceptional host. The space was exactly as described, with plenty of supplies. Communication was stellar. The condo had plenty of extras like clean linens and blankets, there were even additional chargers set up and toiletries if we needed. The beds are comfortable. The bathrooms very clean and updated. Parking right in front. We felt safe and comfortable. This AirBnB is 5 minutes to Windham mountain and minutes from Town. Plenty of places to eat and shop. I highly recommend this Host and property. If we ever go back, we will try to re-book with Cullen.

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub
LOVED staying in this condo. The condo is beautiful and so much room for our group to stay in. We were two families and a grandpa (total was 5 adults, 5 children). Location was incredible. The condo was filled with all the amenities you could need during the stay. Plenty of towels and even toothbrushes if you forget yours. Will definitely stay again.

Cozy Condo w/ Wood Burning Fireplace
My fiancée and I stayed here for our anniversary skiing trip! It’s continently under 5 minutes away from Windham Mountains, and right next to downtown with all its offerings! The condo is cute and makes you feel right at home. A nice massive bed in the bedroom for ample sleeping space, and a working wood burning fire pit. Just a lovely, quiet stay, just what we needed! The hosts were lovely and responsive, giving us locally recommendations which we took!

Cozy Condo @ Jiminy Peak
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.
Home rentals with a private pool

Luxury Retreat in the Catskills
Hands down, our favorite place we've been in a long time. Beautifully decorated, perfect pool, great kitchen, super fast internet - not something you always find in the mountains - and a perfect location close to shops, to hikes, to restaurants. Great, great place. Can't wait to return.

Rhinebeck Country Living with a Modern Twist
Beto and Scott are amazing host! From the complimentary wine to ensuring that we were comfortable by checking in, I couldn't ask for more. My family and I are truly appreciative to have experienced our stay in their home during the holidays. If you're considering renting this, please do (especially in the summer). No complaints!
Magnificent Hudson River Estate with Infinity Pool and Spa
We celebrated thanksgiving with our entire family. So cozy and well equipped. Beds were comfortable. The house was spectacular! Amazing views! So much privacy. The owner, Jean was very accommodating and went out of her way to make sure we had everything. The caretaker Kat was just the same

Magnificent Designer Home - Close To Skiing
Gayle's home was absolutely stunning--the photos do not do it justice, and even they're beautiful. The grounds were just...incredible. The pool area was perfect, as was the garden, which she generously let us pick fresh vegetables from. We saw animals at all times of day, which was a treat for our 5yo. It's a less than 10 min drive to Woodstock and just a few mins to the restaurants in Bearsville. The house is spacious and decor was chic and artsy. Comfortable beds, private spaces for family members + a well-equipped kitchen. We come at the end of every summer to enjoy this area and it's the first house we would return to!!

Catskills Wellness Farm Stay W/ Hot Tub & Sauna
We had a lovely time at Healing Waters Farm. Great location close to Belleayre Mountain. The place itself has everything you need, well stocked kitchen, and lovely clean bathrooms. The property has a calming stream, large swimming hot tub and sauna which we our family enjoyed. Recommend highly for a peaceful getaway.
Quick stats about holiday rentals with a pool in Claverack
Total rentals
20 properties
Nightly prices starting at
$222 AUD before taxes and fees
Total number of reviews
990 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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