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Compare 544 Vacation Homes in Pine Plains with updated reviews, rates, and availability.

Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
6.0 out of 10, 2 reviews
"we where on tour with our band. we like to stay a few minutes from the venue. This was the perfect place only a few minutes to downtown woodstock. We would definitely book again, and the host the host are very awesome. That you again Stacey"
The price is ¥19,675
¥28,489 total
includes taxes & fees
Jul 7 - Jul 8
Beautiful cottage with HOT TUB in Kingston/Woodstock Catskills, Hudson Valley
The Farm at Hyde Park
9.8 out of 10, Exceptional, 49 reviews
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
Historic Hudson Valley 1850 Brick Home
9.0 out of 10, Wonderful, 4 reviews
"Easy to find and great little house. We were very comfortable for the weekend we stayed. When we had a minor issue the host was very responsive."
Historic Hudson Valley 1850 Brick Home
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, 66 reviews
"This was a lovely property in a great waterfront location on a creek. The deck is amazing, the inside is very clean and comfortable, with everything you need and more. Steve was very responsible to any questions we had. Highly recommend."
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, 13 reviews
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, 43 reviews
"This house had so much going for it! Great location, huge space, every bell and whistle imaginable. Very well furnished and equipped. We had a lovely time, and I can't imagine a place we'd have enjoyed more."
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
The Calf Pen
10.0 out of 10, Exceptional, 15 reviews
"Very peaceful place that backs up to a wooded area. The Calf Pen was very clean, plenty of room and has many comforts of home! Glen, the owner, lives on the property but is respectful of your space while being available to answer questions or for a friendly chat. The deck is a wonderful spot to enjoy the sounds of nature and visits from Glen's chickens."
The Calf Pen
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
10.0 out of 10, Exceptional, 7 reviews
"Le Soleil Suite was just as it was pictured. It was very pretty, neat and clean. Sarah provided everything that we needed for our stay and she was very responsive if we had any questions.It was so quiet and peaceful. We truly enjoyed our stay!"
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
Botanical Hideaway: Gorgeous Home w/ Hot Tub & Private Pond
10.0 out of 10, Exceptional, 3 reviews
"This house is even more beautiful in person. From the high-quality dishes to the beautiful design, sauna, outdoor space and fenced-in backyard, it was a great vacation for all of us, including the dog. They were working on the barn during our stay but management was very responsive and the workers were so nice. We can't wait to see what they turn the barn into! Location was convenient to the ski area (to visit friends about 30 minutes away) and my in-laws who were also about 25 minutes away. We...
Botanical Hideaway: Gorgeous Home w/ Hot Tub & Private Pond
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, 32 reviews
"Great stay. A short walk to everything the lake has to offer."
Cozy Retreat on Copake Lake in our Charming Home
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, 11 reviews
"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"
The price is ¥188,880
¥291,151 total
includes taxes & fees
Jun 24 - Jun 25
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, 10 reviews
"The property was gorgeous, the house large enough to accommodate our group. The kitchen was well stocked. We used the pool, hot tub, fire pit, and pool table. The indoor and outdoor speakers were a nice touch. I would definitely recommend this home I had to reach out to our host 2 days before check in to find out how to get in- usually that is communicated earlier than that. I had informed the host that we were going to have a luncheon for 10 additional people after the memorial service and was...
Spacious restored Victorian w/ wraparound porch
Historic Kingston 1800s Waterfront Townhouse - / Backyard / BKLYN Loft / Modern
9.8 out of 10, Exceptional, 25 reviews
"Loved everything about the place. Exactly as represented, in a really cool and relatively quiet neighborhood. If stairs bother you then that might be the only downside as the inner staircase is pretty steep but has excellent railings and safety glass."
Historic Kingston 1800s Waterfront Townhouse - / Backyard / BKLYN Loft / Modern
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, 128 reviews
"Our stay at The Barn in New York was unforgettable. This luxury home, converted from a barn and situated at the end of a back road, is surrounded by 50 acres of picturesque fields and has every amenity. With many restaurants a short drive away and only 20 minutes to Great Barrington, MA, and Hudson, NY, we were never short on dining options and The Prairie Whale was our favorite and also dog friendly. The area offered endless adventures with hiking trails, antique stores, galleries, and outdoor...
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, 7 reviews
"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"
The price is ¥25,027
¥52,657 total
includes taxes & fees
Jun 30 - Jul 1
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
4-bedrooms with gym+spa access in the Village of Saugerties 1/4 mile from HITS!
9.0 out of 10, Wonderful, 11 reviews
"Loved the location! Very quiet and clean. Will stay here again!"
4-bedrooms with gym+spa access in the Village of Saugerties 1/4 mile from HITS!
Esopus Creek modern Tiny house Retreat!
8.0 out of 10, Very Good, 2 reviews
"This tiny home in the forest was the perfect stop on my week-long road trip through NY. It was easy to find, despite being tucked away. The home has every amenity you could need."
The price is ¥24,397
¥34,452 total
includes taxes & fees
Jun 17 - Jun 18
Esopus Creek modern Tiny house Retreat!
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, 14 reviews
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
Golf Car ride to HITS! Saugerties home with gym+spa access.
9.2 out of 10, Wonderful, 11 reviews
"Just a work stay for us"
Golf Car ride to HITS! Saugerties home with gym+spa access.
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, 107 reviews
"Our party of four adults found ample space to spread out and relax at this property. There are quite a few stairs to access all three stories, including the main living space on the second story and the four bedrooms on the third story. The kitchen is well equipped and there is a charcoal grill (bring your own charcoal). There is a very nice deck overlooking the lovely and sprawling grounds below the house. A fire pit was situated behind the house. There is a balcony and patio also off the...
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
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See all available properties in Pine Plains
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Pine Plains

Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, 74 reviews
"Only stayed one night, but would have loved to stay for one week! Beautiful grounds and our host, Steven, was super welcoming and greeted us once we arrived to check us in. Local cat also greeted us once we arrived (if you’re driving, check under your car before backing out!)"
The price is ¥19,738
¥22,171 total
includes taxes & fees
Jun 17 - Jun 18
Micosta Leisure Inn
The Farm at Hyde Park
9.8 out of 10, Exceptional, 49 reviews
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very Good, 37 reviews
"Our trip was amazing. We do it again again and again"
The price is ¥19,675
¥19,675 total
includes taxes & fees
Jun 19 - Jun 20
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pine Plains Vacation Homes information

Number of reviews
507
Accommodation
544 Vacation Homes
Lowest Price
¥19,675
Highest Price
¥188,880

Recent reviews of Pine Plains hotels
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