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

Spencertown Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Spencertown vacation rentals

Exterior

1. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (161 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is ￥21,334
￥23,893 total
includes taxes & fees
Aug 2 - Aug 3
Micosta Leisure Inn
Property grounds

2. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥39,350
￥63,640 total
includes taxes & fees
Aug 9 - Aug 10
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,036 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is ￥15,749
￥21,108 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
Terrace/patio

4. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is ￥43,285
￥55,029 total
includes taxes & fees
Aug 12 - Aug 13
BLUSH: Boutique TINY home*private spa*walk to town
Dining

5. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is ￥41,711
￥53,075 total
includes taxes & fees
Aug 3 - Aug 4
Sugar Shack - 300 square feet of pure sweetness.
Exterior

6. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ￥49,581
￥90,436 total
includes taxes & fees
Aug 9 - Aug 10
Gorgeous Mountain Views Retreat: Family & Nature
Interior

7. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥34,652
￥52,243 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Riverside Berkshires Retreat
Interior

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥40,137
￥66,283 total
includes taxes & fees
Aug 12 - Aug 13
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior detail

9. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is ￥48,637
￥106,126 total
includes taxes & fees
Aug 2 - Aug 3
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
TV, fireplace, printers

10. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥89,529
￥209,539 total
includes taxes & fees
Aug 6 - Aug 7
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
House (3 Bedrooms) | Front of property

11. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Coffee/tea maker, fridge, microwave, oven

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,498
￥64,348 total
includes taxes & fees
Aug 12 - Aug 13
Home in Great Barrington
Pool

13. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.0 out of 10, Wonderful, (4 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is ￥34,313
￥63,287 total
includes taxes & fees
Sep 1 - Sep 2
Hudson NY’S Country Serenity Guest Suite.
Desk, iron/ironing board, WiFi, bed sheets

14. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥24,869
￥31,379 total
includes taxes & fees
Aug 2 - Aug 3
The Brooks Motel: Exceptional Suite
Outdoor dining

15. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is ￥42,183
￥88,446 total
includes taxes & fees
Aug 4 - Aug 5
NEW RENO Historic Creamery in Berkshires w/hot tub
TV, fireplace, DVD player, books

16. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is ￥29,749
￥117,761 total
includes taxes & fees
Aug 9 - Aug 10
Mtn-View Retreat in Huson Valley: Great for Groups
Property grounds

17. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is ￥15,441
￥20,818 total
includes taxes & fees
Aug 3 - Aug 4
All comforts of home
Terrace/patio

18. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
The price is ￥29,434
￥57,823 total
includes taxes & fees
Aug 3 - Aug 4
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Coffee/tea maker, fridge, microwave, oven

19. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very Good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
Cozy 1-bedroom studio in serene Great Barrington with AC
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 Spencertown Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Hotel is beautifully decorated, I stayed one night and it was perfect. Dinner was delicious and the tea and cookies outside were wonderful. I saw people enjoying beautiful cocktails too. Overall the room was beautiful and showering with Le Labo products was a great way to end the day!"
Yekaterina 1-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Spencertown

Search for holiday rentals in Spencertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Spencertown using one of the methods below:

  • View our selection of featured holiday rentals in Spencertown
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Look no further and take a look at our great range of rental properties in Spencertown!

Frequently asked questions

Can I find a vacation rental in Spencertown?

Yes, you can find vacation rentals close to popular points of interest in Spencertown, or you can go with a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Spencertown has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Spencertown is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Spencertown?

Expedia has 3 vacation rentals for your stay in Spencertown.

What’s there to see and do in Spencertown?

Explore the area and family-friendly sights such as Bousquet Ski Area, or get out into nature at a spot like Queechy Lake. The Mac-Haydn Theatre and Berkshire Botanical Garden are a couple of places you'll find in the larger area.

What’s a vacation rental in Spencertown like?

A vacation rental is a private property you can book for a couple of days or more in Spencertown. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.