Woodstock Holiday Rentals, New York: Private House Rentals

A calm lake with a sunset reflecting on the water, surrounded by forested hills.

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Go beyond your typical stay in Woodstock

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Our top choices for Woodstock hotels

A wooden cabin with large windows overlooking a forested area with a waterfall.

A wooden deck with outdoor seating, a wooden deck with a view of the interior, and a wooden deck with a view of the exterior.

A two-story wooden house with a stone retaining wall, a stone pathway, and a small garden with various plants.

A modern bedroom with a wooden bed, a desk, and large windows.

1. Woodstock Way Hotel

Woodstock

Vannetta

฿10,956

฿13,579 total

includes taxes & fees

20 Oct - 21 Oct

A living room with a fireplace, green sofa, and a leopard print armchair.

A modern bedroom with a large bed, a bedside table with a lamp, a view of greenery outside, and a checkered rug.

A wooden deck with outdoor seating and a house in the background.

A white house with a green door, black trim, and a porch with a lantern.

2. Twin Gables of Woodstock

Woodstock

Coleen

฿4,828

฿5,408 total

includes taxes & fees

9 Nov - 10 Nov

A white house with a porch, surrounded by lush greenery and two green Adirondack chairs.

A spacious living room with a fireplace, two sofas, a coffee table, and a TV mounted above the fireplace.

A cozy living room with a fireplace, comfortable seating, and a dining area with a table set for four.

A picnic setup with a table, food, drinks, and binoculars by a stream.

3. The Woodstock Inn on the Millstream

Woodstock

Carolyn

฿7,678

฿8,600 total

includes taxes & fees

13 Oct - 14 Oct

A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.

A wooden sign with the text "Mitchell Manor" hanging from a building.

A modern kitchen with a wooden island, black cabinets, and a built-in refrigerator. There are hanging plants, a coffee machine, and shelves with dishes and utensils.

A two-story house with a porch, a sign for 'The Herwood Inn', and a well-maintained lawn.

4. The Herwood Inn

Woodstock

Diana

฿9,811

฿10,988 total

includes taxes & fees

22 Oct - 23 Oct

A serene garden with a stone pathway, a small bridge, and a bench.

A hallway with a framed portrait on the wall, a door to the right, and a window on the left.

A rustic wooden pergola in a garden with a house in the background.

A room with a large tapestry, two wicker chairs, a small table, and a globe lamp.

5. Morning Glory B n B Woodstock NY

Woodstock

Lucian

฿7,343

฿8,224 total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with two beds, a desk, and a large window.

A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

An outdoor patio with a round table and orange chairs, a black metal fence, and string lights.

A stone building with multiple windows and a door, situated on a street corner.

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

Lake Katrine

Timothy

฿4,091

฿4,582 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor patio with a fire pit, seating, and a building in the background.

A modern hotel room with a grey sofa, an orange armchair, a small wooden table, and a large window with sheer curtains.

A Courtyard by Marriott hotel with a modern facade, large windows, and a well-maintained entrance area.

A modern cafe with a wooden counter, bar stools, and a menu board above the counter.

7. Courtyard by Marriott Kingston

Kingston

George

฿4,247

฿4,756 total

includes taxes & fees

25 Oct - 26 Oct

A spacious lobby with a fireplace, comfortable seating, and large windows.

A breakfast buffet setup with a variety of food items, including bread, cereal, and fruits, in a modern hotel dining area with striped chairs and a large window.

A multi-story hotel with a well-lit entrance, a flag, and a sign indicating it is a Marriott Residence Inn.

An indoor swimming pool with lounge chairs and a view of the outside.

8. Residence Inn by Marriott Kingston

Kingston

Lamisa

฿4,493

฿5,032 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.

An indoor swimming pool with clear water, a 5 feet deep sign, and a tiled floor.

A candy store with shelves of various treats and a sign that reads "TREATS".

A Hampton Inn hotel with a modern facade, multiple entry points, and a well-lit entrance.

9. Hampton Inn Kingston

Kingston

Jennifer

฿4,179

฿4,681 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.

A modern house with a sloped roof, large windows, and a well-maintained lawn.

A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.

10. AutoCamp Catskills

Saugerties

Raquel

฿4,389

฿6,230 total

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with a glass ceiling, indoor seating, and a brick wall.

A restaurant with booths, tables, and a bar area.

A bar area with a long counter, multiple bar stools, and a television mounted above the bar.

11. Kingston Regency Inn

Kingston

Stephen

฿4,225

฿5,192 total

includes taxes & fees

2 Nov - 3 Nov

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

A historic hotel with a prominent tower and a brick facade.

A bar with a patterned floor, bar stools, and a bar counter with taps.

12. Diamond Mills Resort

Saugerties

฿8,912

฿10,819 total

includes taxes & fees

12 Oct - 13 Oct

A restaurant with orange seating, white tablecloths, and potted plants.

A cozy living room with a wood-burning stove, wicker furniture, and a bookshelf.

A room with a red accent wall, a large potted plant, and a small stool.

A hotel room with a large window, two blue armchairs, a round table with a plant, and a bed with a white blanket.

13. Hotel Kinsley

Stockade District

Daile

฿7,952

฿10,354 total

includes taxes & fees

9 Nov - 10 Nov

An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.

A reception area with a wooden reception desk, a television mounted on the wall, a blue sofa, and a fireplace with plants.

A hotel room with a bed, a desk, a sofa, and two lamps.

A hotel room with a bed, desk, chair, TV, and kitchenette.

14. Comfort Inn Saugerties

Saugerties

John

฿4,532

฿5,075 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A hotel room with two beds, a TV, a dresser, and a door leading to another room.

A restaurant with a bar area, wooden booths, and a coffee machine.

A Howard Johnson Inn with a beige facade, red trim, and a clear blue sky with clouds.

15. Howard Johnson by Wyndham Saugerties

Saugerties

Shirley

฿3,682

฿4,123 total

includes taxes & fees

2 Nov - 3 Nov

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

A modern breakfast area with a coffee machine, cereal, and bakery options.

A modern lobby with a reception desk, seating area, and a dining section.

A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.

16. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Cindy

฿4,258

฿4,769 total

includes taxes & fees

8 Nov - 9 Nov

A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

A well-maintained garden with a red bridge, a welcome sign, and a building with a gabled roof.

A spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

A couple standing on a wooden deck overlooking a landscaped garden with a river view.

17. Emerson Resort & Spa

Mount Tremper

Ashley

฿6,002

฿6,722 total

includes taxes & fees

1 Nov - 2 Nov

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

A modern hotel lobby with a wooden floor, a reception desk, two patterned armchairs, a chandelier, and a view of the outdoors through a glass door.

A bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

18. Hotel Mountain Brook

Tannersville

Kristen

฿8,181

฿8,836 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with two beds, a green wardrobe, a mirror, a fireplace, and a desk with a lamp.

A historic white building with a porch, American flags, and a sign for Beekman Arms Inn.

A covered outdoor dining area with tables set for two, featuring white tablecloths and black metal chairs.

A covered outdoor dining area with tables set for a meal, surrounded by columns and large windows.

19. Beekman Arms and Delamater Inn

Rhinebeck Village

Victoria and Scott

฿5,100

฿5,769 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with two beds, a nightstand, a lamp, and two framed pictures on the wall.

A hotel lobby with a reception desk, two armchairs, a small table, and a lamp.

A multi-story hotel with a flat roof, large windows, and a brick facade.

A bathroom with a walk-in shower, grab bars, and a white tiled wall.

20. Super 8 by Wyndham Kingston

Kingston

Simon

฿2,822

฿3,160 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Woodstock attractions

Woodstock Music Shop

9.6/10 (18 reviews)

Vinyl paradise awaits at Woodstock Music Shop with its curated collection spanning countless genres. Engage with knowledgeable staff who can guide you to musical treasures among the rare albums and handcrafted vinyl art.

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Overlook Mountain Trailhead

9.6/10 (34 reviews)

Hike through ruins of the historic Overlook Mountain House before reaching a restored fire tower. Climb to the summit for breathtaking 360-degree views of the Hudson Valley and Catskill Mountains.

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Karma Triyana Dharmachakra Monastery

10.0/10 (12 reviews)

This Tibetan Buddhist monastery showcases a magnificent two-story Buddha statue and serves as the Gyalwang Karmapa's North American seat. Join free weekend guided tours to learn about sacred traditions.

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Bearsville Theater

You can get tickets for a performance at Bearsville Theater during your trip to Woodstock. Amble around this relaxing area's forests or experience its art scene.

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Colony

This historic Woodstock venue blends rustic charm with live music in an intimate setting. Enjoy performances in the vintage ballroom or unwind in the beer garden with dinner and craft cocktails.

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Woodstock Public Library

8.8/10 (25 reviews)

The historic Woodstock Public Library District has served as a community learning hub since 1913. Currently closed for relocation until 2025, visitors should check their website for pop-up events and digital services.

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Tinker Street Tavern

Tinker Street Tavern is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's forests or experience its art scene.

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Woodstock Golf Club

9.0/10 (2 reviews)

This historic nine-hole golf course designed by Tom Bendelow offers a serene challenge among mature trees. Members and their guests enjoy bent-grass fairways and comprehensive instruction from April through October.

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Learn more about Woodstock

Artists and musicians have shaped this Catskill mountain town since the legendary 1969 festival that wasn't actually held here. Spend mornings browsing quirky boutiques and galleries on Tinker Street before hiking nearby trails to swimming holes locals might share if you ask nicely.

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A green building with a sign reading "Woodstock Playhouse" and a white RV parked in front.

Top Woodstock Hotel Reviews

Beekman Arms and Delamater Inn

8/10 Good

"This was my first time at this property. My room was not in the Beekman Arms but in its sister property a few blocks away. The room was large and nicely decorated, it was very clean and the bed was comfortable. The bathroom was very nice and soap, shampoo and towels were supplied in abundance. Breakfast was included and consisted of all sorts of breads, fruit, yogurt, hard boiled eggs, juiced coffee and teas. This was served in a separate building near the residential building Our room was on the third floor so the lack of an elevator pushed my 94 year old body a bit. I would definitely come back to the Beeckman Arms but next time I’ll request a downstairs room."

AutoCamp Catskills

8/10 Good

"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"

Kingston Regency Inn

10/10 Excellent

"Good"

The Herwood Inn

10/10 Excellent

"Love the room, it had so much feel and character. Very welcoming host that chatted with us about Woodstock and restaurant recs. Super cute, unique wooden hot tub that is very comfortable and feels like you are sitting in a giant barrel."

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"Good breakfast. Friendly helpful staff."

Pocketbook Hotel and Bath

10/10 Excellent

"Beautiful building. Glad to see it repurposed."

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"Always a nice stay."

Twin Gables of Woodstock

10/10 Excellent

"Loved our stay at Twin Gables! It's a very bright, well-kept property within walking distance of lots of dining, shopping & a park with a nice hiking loop. I was surprised at how quiet it was, despite it being full the last 2 nights of our 4 night stay. Our room faced the street but that end of the street was quiet so there was no issue. The clothes rack and shelves in the room and the bench shelf in the bathroom were helpful for having a place to put things. Good shower pressure and hot water. The included breakfast was simple but convenient and helped us get out the door to our adventures. I would definitely stay here again."

St. Charles Hotel

8/10 Good

"The St. Charles hotel is a good place to stay if you are looking for a great location to stay. It's within walking distance of restaurants and close to places to visit. However the WiFi network does kick out a lot."

More cheap stays in Woodstock

Quality Inn Hyde Park Poughkeepsie North

4142 Albany Post Rd Hyde Park NY

฿2,423

฿2,741 total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,001 reviews)

Americas Best Value Inn New Paltz

7 Terwilliger Ln New Paltz NY

฿3,520

฿3,942 total

1 Nov - 2 Nov

includes taxes & fees