Spencertown Holiday Rentals, New York: Private House Rentals

A diner with a green roof and a red barn in the background.

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Our top choices for Spencertown hotels

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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

Great Barrington

Bruce

Rp3.499.418

Rp3.908.850 total

includes taxes & fees

5 Oct - 6 Oct

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A bar with wooden floors and shelves filled with bottles.

2. The Red Lion Inn

Stockbridge

Stephan

Rp3.196.303

Rp4.463.566 total

includes taxes & fees

19 Oct - 20 Oct

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A Quality Inn sign, a brick building, and a parking lot with cars.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

3. Quality Inn Great Barrington

Great Barrington

Joan

Rp1.818.778

Rp2.031.575 total

includes taxes & fees

20 Oct - 21 Oct

A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

A wooden deck with a dog silhouette against a backdrop of autumn foliage.

A wooden wall with a white pendant light fixture.

4. Prospect Berkshires

Egremont

Conor

Rp7.525.048

Rp9.008.022 total

includes taxes & fees

1 Oct - 2 Oct

A red building with a sign reading "Shaker Mill Inn."

A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

5. Shaker Mill Inn

West Stockbridge

Mervin

Rp3.218.062

Rp3.530.213 total

includes taxes & fees

1 Oct - 2 Oct

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

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

Great Barrington

Maria Dulce

Rp2.139.739

Rp2.390.035 total

includes taxes & fees

19 Oct - 20 Oct

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

7. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

Rp2.542.693

Rp2.840.188 total

includes taxes & fees

25 Oct - 26 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

8. The Yankee Inn

Lenox

William

Rp1.941.948

Rp2.169.228 total

includes taxes & fees

27 Oct - 28 Oct

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

9. Berkshires Untold

Lenox

Madhavi R

Rp2.888.324

Rp3.226.259 total

includes taxes & fees

26 Oct - 27 Oct

A wooden deck with white railings and hanging flower baskets.

A two-story building with a balcony, a red door, and a staircase leading to the second floor.

A bathroom with a bathtub, toilet, and sink. There is a shower curtain, a towel rack, and a hairdryer.

A hotel room with two queen beds, a desk, a chair, a lamp, and a window with curtains.

10. Chatham Travel Lodge

Old Chatham

andrew

Rp2.010.839

Rp2.251.924 total

includes taxes & fees

1 Oct - 2 Oct

A large house with a balcony and a grassy yard.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

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

A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.

11. The Little Lion

Great Barrington

Lidia

Rp1.861.033

Rp2.078.774 total

includes taxes & fees

18 Oct - 19 Oct

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

A house with a stone patio and wooden stools.

A wooden fire pit surrounded by six Adirondack chairs in a forested area.

12. Little Cat Lodge

Copake Falls

Kees

Rp3.220.397

Rp3.606.845 total

includes taxes & fees

4 Oct - 5 Oct

13. Berkshire Travel Lodge

Austerlitz

Kris

Rp1.213.335

Rp1.358.957 total

includes taxes & fees

4 Oct - 5 Oct

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

14. Inn at Silver Maple Farm

East Chatham

Erdem

Rp4.387.364

Rp4.913.848 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

15. Quality Inn Lee - Lenox South

Lee

Christine

Rp1.971.617

Rp2.202.296 total

includes taxes & fees

20 Oct - 21 Oct

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A motel with a parking lot and several cars parked.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

16. Monument Mountain Motel

Great Barrington

Victor

Rp1.229.900

Rp1.373.748 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

17. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

Rp1.901.713

Rp2.124.214 total

includes taxes & fees

26 Oct - 27 Oct

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

18. Berkshire Mountain Lodge

Pittsfield

Jay

Rp1.431.276

Rp2.000.432 total

includes taxes & fees

1 Oct - 2 Oct

A building with a porch and multiple windows, surrounded by purple flowers.

A living room with a sofa, armchair, coffee table, and a patterned rug.

A café with a display case, a frozen food section, and a marketplace sign.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

19. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Jared

Rp2.103.777

Rp2.701.465 total

includes taxes & fees

18 Oct - 19 Oct

A group of people performing yoga in an outdoor setting with grass and trees.

A hotel room with a bed, two chairs, a small table, and a lamp.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

20. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

Rp1.107.445

Rp1.214.773 total

includes taxes & fees

1 Oct - 2 Oct

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Venture to Berkshire Botanical Garden and Norman Rockwell Museum—just two of the sights around Spencertown.

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Top Spencertown Hotel Reviews

Berkshires Untold

8/10 Good

"A very good place to stay"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"This was a nice clean convenient hidden gem. Situated on the water, a little cool right now , but the beginning of fall follege was very pretty. Staff was polite and helpful. I would return."

Quality Inn Lee - Lenox South

10/10 Excellent

"Very sweet desk clerk answered my question about late arrival quickly and cheerfully."

Quality Inn Great Barrington

10/10 Excellent

"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."

The Red Lion Inn

10/10 Excellent

"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."

The Yankee Inn

10/10 Excellent

"Nice room. Exceptionally clean. Great staff"

St. Charles Hotel

8/10 Good

"The room was clean and modern and the staff were friendly and professional. Parking was close and ample."

voco James Newbury Hudson Valley by IHG

10/10 Excellent

"The property is set in a small quaint area overlooking the river. The hotel and additional buildings are really pretty and our room was huge and comfortable for three people. The staff were attentive, the beds were comfortable, and the shower hot. We were going to a show at the Basilica Hudson so although it was a short stay, it was wonderful and would highly recommend. We didn’t partake in the restaurant, live music or breakfast, but all seemed to be a great addition."

More cheap stays in Spencertown