Pine Plains Holiday Rentals, New York: Private House Rentals

A rustic barn surrounded by autumn foliage on a hillside.

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Go beyond your typical stay in Pine Plains

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Our top choices for Pine Plains hotels

1. Inn at Pine Plains

Pine Plains

Mary

7.143.125 ₫

8.080.661 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Desk, blackout curtains, iron/ironing board, free WiFi

2. Courtyard by Marriott Kingston

Kingston

Ana

3.291.127 ₫

3.686.062 ₫ total

includes taxes & fees

20 Sept - 21 Sept

3. Residence Inn by Marriott Kingston

Kingston

Lamisa

3.715.998 ₫

4.161.918 ₫ total

includes taxes & fees

20 Sept - 21 Sept

4. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

3.350.775 ₫

3.742.815 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Penthouse (Penthouse Suite) | Premium bedding, in-room safe, desk, soundproofing

5. Interlaken Inn & Resort

Lakeville

Stacie

6.213.220 ₫

7.145.203 ₫ total

includes taxes & fees

17 Sept - 18 Sept

Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillow-top beds, desk

6. Quality Inn Great Barrington

Great Barrington

Kimberly

2.689.711 ₫

3.004.268 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Superior Room, 1 King Bed | Minibar, iron/ironing board, free WiFi, bed sheets

7. the Alander

Copake

Phil

3.753.387 ₫

4.203.792 ₫ total

includes taxes & fees

17 Sept - 18 Sept

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Bruce

5.056.034 ₫

5.647.590 ₫ total

includes taxes & fees

20 Sept - 21 Sept

9. Beekman Arms and Delamater Inn

Rhinebeck Village

Mariya

3.487.143 ₫

3.944.831 ₫ total

includes taxes & fees

23 Sept - 24 Sept

Suite, 1 King Bed, Non Smoking, Jetted Tub | Premium bedding, in-room safe, desk, iron/ironing board

Premium bedding, in-room safe, desk, iron/ironing board

10. Kingston Regency Inn

Kingston

kyle

3.506.625 ₫

4.207.120 ₫ total

includes taxes & fees

27 Sept - 28 Sept

11. Little Cat Lodge

Copake Falls

Kees

4.652.122 ₫

5.210.377 ₫ total

includes taxes & fees

17 Sept - 18 Sept

12. Hampton Inn Kingston

Kingston

stephen

3.783.821 ₫

4.237.880 ₫ total

includes taxes & fees

27 Sept - 28 Sept

13. Howard Johnson by Wyndham Saugerties

Saugerties

Richard

3.610.525 ₫

4.043.788 ₫ total

includes taxes & fees

21 Sept - 22 Sept

Premium bedding, in-room safe, desk, laptop workspace

14. Holiday Inn Express & Suites Kingston-Ulster by IHG

Lake Katrine

Bailey

3.612.054 ₫

4.045.500 ₫ total

includes taxes & fees

27 Sept - 28 Sept

Room (3) | Iron/ironing board (on request), free WiFi

Room (5) | Iron/ironing board (on request), free WiFi

15. The Millerton Inn

Millerton

Yiu Chung Benjamin

6.522.322 ₫

7.378.377 ₫ total

includes taxes & fees

22 Sept - 23 Sept

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

16. Monument Mountain Motel

Great Barrington

Analisia

1.998.776 ₫

2.232.811 ₫ total

includes taxes & fees

17 Sept - 18 Sept

Bluejay Cache | Desk, iron/ironing board (on request), free WiFi, bed sheets

17. Cornwall Inn and Lodge

Cornwall Bridge

Richard T

5.496.310 ₫

6.320.757 ₫ total

includes taxes & fees

17 Sept - 18 Sept

Full-sized fridge, microwave, stovetop, cookware/dishes/utensils

Studio, 2 Queen Beds, Kitchenette | Free WiFi, bed sheets

18. The Lagrange Inn & Extended Stay

Pleasant Valley

Anastasiya

3.393.011 ₫

3.838.343 ₫ total

includes taxes & fees

28 Sept - 29 Sept

John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

19. The White Hart

Salisbury

William

8.945.790 ₫

10.287.659 ₫ total

includes taxes & fees

20 Sept - 21 Sept

In-room safe, desk, laptop workspace, blackout curtains

20. Super 8 by Wyndham Kingston

Kingston

Simon

2.186.722 ₫

2.449.129 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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Stay near popular Pine Plains attractions

Stissing Lake Park

Stissing Lake Park offers a serene lakeside escape with clear waters perfect for swimming and fishing. Families gather at picnic areas surrounded by natural beauty, creating a peaceful retreat from everyday life.

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Thompson Pond

8.0/10 (1 review)

This 15,000-year-old glacial kettle pond offers a peaceful 2.7-mile trail through diverse ecosystems. Bring binoculars to spot some of the 160 bird species that inhabit this National Natural Landmark.

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The Stissing Center

This restored historic venue hosts diverse performances from music to theatre in Pine Plains, New York. Immerse yourself in intimate cultural experiences where historic charm meets modern artistic expression.

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Gallatin Town Hall

Gallatin Town Hall serves as the administrative heart of the community, hosting public meetings and town services. Monthly board meetings are held on the third Tuesday at 6:30 PM.

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Pine Plains Library

This welcoming community library offers diverse programmes and a rich collection. Enjoy comfortable reading areas and free Wi-Fi while exploring local history resources with help from knowledgeable staff.

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Learn more about Pine Plains

Hike the trails of Stissing Mountain for panoramic views of this charming Hudson Valley town and its surrounding countryside. Spend afternoons exploring local farm stands or enjoying the peaceful waters of Stissing Lake with a picnic from Main Street businesses.

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Top Pine Plains Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Everything was so smooth, from the detailed map and heads up of possible cell service interruptions, to the check in and check out process, housekeeping request, and the ease of communication via text. It was a perfect getaway, minimal interruptions, yet easy to reach with quick responses. Although I could tell there were other guests in cabins nearby because I would see parked cars, it was so quiet that I felt like I was truly there alone! They thought of everything as far as cookware, plates, cups for cold and hot drinks, and utensils. S’mores, snacks, water, coffee, tea, and use of firepit/firewood were all complimentary. There’s a fridge but no microwave which I was not expecting but useful to know. Bring seasoning if you plan to cook. Bring mosquito repellant. It was weird not having a sink in the bathroom but it wasn’t a big deal for me. Would definitely book again!"

Beekman Arms and Delamater Inn

10/10 Excellent

"Cozy, comfy. Relaxing. Roomy. Even had a bookshelf loaded with paperbacks! Hand hardcover too!"

Rhinebeck Village Inn

8/10 Good

"It was fine, thanks."

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent

"The view from my room was of a wooded area complete with a friendly Marmot. Staff was a quiet but always close-at-hand and efficiently took care of every request promptly and we'll. High recommendation."

Kingston Regency Inn

10/10 Excellent

"Quiet, clean,helpful staff."

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable but the pillows not so great but clean and quiet."

St. Charles Hotel

10/10 Excellent

"Overall a good experience at a good price."

Inn at Pine Plains

10/10 Excellent

"I had a lovely stay! Plan to return another time."

Howard Johnson by Wyndham Saugerties

8/10 Good

"We stayed here once before. Staff were nice. Room was okay. Kinda old. But okay for a short stay. Internet was in and out. Bathroom water never got real hot for showers. Toilet was very low... my knees were in my mouth. The toilet bowl seat was close to broken. We MAY come back if necessary. Hopefully, some of our current concerns will be remedied. Thanks"

More cheap stays in Pine Plains

Quality Inn Hyde Park Poughkeepsie North

4142 Albany Post Rd Hyde Park NY

2.098.370 ₫

2.373.781 ₫ total

7 Oct - 8 Oct

includes taxes & fees