Pine Plains Vacation Rentals

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Browse Select Pine Plains Vacation Homes

Our top choices for Pine Plains vacation homes

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

10.0 out of 10, Exceptional, (4)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
The price is CA $80
CA $315 total
includes taxes & fees
Sep 10 - Sep 11
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (26)
"Perfect cozy little spot for 2. Centrally located to explore surrounding areas"
The price is CA $104
CA $345 total
includes taxes & fees
Sep 10 - Sep 11
Campfire Cottage: Fireplace, fire pit & no chores!

Retro Retreat: renovated 2BR, desk, no chore list!

9.6 out of 10, Exceptional, (11)
"Very clean and nice inside. Host was very communicative. "
The price is CA $101
CA $384 total
includes taxes & fees
Sep 10 - Sep 11
Retro Retreat: renovated 2BR, desk, no chore list!

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

10.0 out of 10, Exceptional, (3)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
The price is CA $201
CA $337 total
includes taxes & fees
Sep 4 - Sep 5
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
10.0 out of 10, Exceptional, (2)
"The property was great and the house was huge even for all 12 of us "
The price is CA $246
CA $1,020 total
includes taxes & fees
Aug 24 - Aug 25
CT Gate House Goshen CT, Gate House Goshen CT

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is CA $153
CA $202 total
includes taxes & fees
Aug 24 - Aug 25
Sioux Tipi on Chloe's Lake

Peaceful Cabin w/ Fire Pit & Creek Access

10.0 out of 10, Exceptional, (7)
"Great little space , clean, comfortable and equipped with everything I needed for a nice weekend! Would stay again if ever I return to the area ."
The price is CA $115
CA $321 total
includes taxes & fees
Sep 9 - Sep 10
Peaceful Cabin w/ Fire Pit & Creek Access

All the comforts of home

9.0 out of 10, Wonderful, (24)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is CA $148
CA $197 total
includes taxes & fees
Aug 24 - Aug 25
All the comforts of home

Mid Century Modern Studio w/ Full Kitchen - Newly Built

9.0 out of 10, Wonderful, (2)
"Super cute, clean, and convenient for our quick trip to The Millbrook School."
The price is CA $271
CA $346 total
includes taxes & fees
Aug 28 - Aug 29
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Cozy Bedroom With Fireplace

The price is CA $207
CA $281 total
includes taxes & fees
Aug 27 - Aug 28
Cozy Bedroom With Fireplace

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is CA $258
CA $707 total
includes taxes & fees
Aug 24 - Aug 25
Perfect House In Hillsdale, Brings Friends & Fam

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is CA $262
CA $421 total
includes taxes & fees
Sep 1 - Sep 2
Home in Great Barrington

Charming studio in Welcoming Saugerties

The price is CA $157
CA $350 total
includes taxes & fees
Sep 8 - Sep 9
Charming studio in Welcoming Saugerties

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (46)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is CA $207
CA $336 total
includes taxes & fees
Aug 24 - Aug 25
Esopus Creek modern Tiny house Retreat!

Grand Opening Special - Quiet 2-Bedrm in the Village

8.0 out of 10, Very good, (1)
"Lynn’s apartment was convenient, comfortable and charmingly old-fashioned. Great beds! Our only complaint is a frequent one for us at rental properties- way too much Febreeze! I detest the odor and I don’t think it really cleans anything….."
The price is CA $228
CA $495 total
includes taxes & fees
Sep 8 - Sep 9
Grand Opening Special - Quiet 2-Bedrm in the Village

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

10.0 out of 10, Exceptional, (4)
"This cabin is so cute we had a relaxing time , will return"
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Brand New House w gated backyard that is located right at the Saugerties Village

10.0 out of 10, Exceptional, (35)
"Newly remodeled and in a nice quiet neighborhood next to a store. Walking distance to downtown shops and restaurants."
The price is CA $263
CA $586 total
includes taxes & fees
Sep 15 - Sep 16
Brand New House w gated backyard that is located right at the Saugerties Village

Charming Retreat at Stone Hill Estate – Nature Meets Luxury

10.0 out of 10, Exceptional, (1)
"Great experience overall! Property is beautiful and the guest home is situated nicely with access to the backyard and pond. Everything was very clean and well kept with everything in the home that we needed. The hosts were very kind and welcomed us making the stay enjoyable. Would recommend. "
The price is CA $555
CA $987 total
includes taxes & fees
Sep 7 - Sep 8
Charming Retreat at Stone Hill Estate – Nature Meets Luxury

Catskill Stay w/ Deck & Fire Pit

6.0 out of 10, (1)
"Nice house"
The price is CA $190
CA $597 total
includes taxes & fees
Aug 25 - Aug 26
Catskill Stay w/ Deck & Fire Pit

Double the Fun: Two Houses, Shared Yard & Fire Pit

10.0 out of 10, Exceptional, (4)
"Contemporary and clean. Totally attentive host."
The price is CA $285
CA $799 total
includes taxes & fees
Sep 10 - Sep 11
Double the Fun: Two Houses, Shared Yard & Fire Pit
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.
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Top Pine Plains Hotel Reviews