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Spencertown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Spencertown vacation rentals

Exterior
Micosta Leisure Inn

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (132)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is ￥20,246
￥22,677 total
includes taxes & fees
Dec 15 - Dec 16
Micosta Leisure Inn
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is ￥23,418
￥51,373 total
includes taxes & fees
Dec 18 - Dec 19
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Beach
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is ￥15,005
￥32,577 total
includes taxes & fees
Dec 17 - Dec 18
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is ￥25,241
￥41,595 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Home in Great Barrington
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,285
￥20,607 total
includes taxes & fees
Dec 15 - Dec 16
All comforts of home
Property grounds
All the comforts of home

Vacation Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (28)
"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! "
United States
Marisa P.
The price is ￥16,547
￥22,024 total
includes taxes & fees
Dec 15 - Dec 16
All the comforts of home
Outdoor dining
Charming Cottage in the Heart of Catskill & Pet Friendly

Cottage in Catskill

Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (18)
"We had a wonderful time at the Catskill Nook. Everything was great and the hosts were amazing. Well located, walking distance to everything and pet friendly. The flowers from our hosts were gorgeous. We had a blast. "
United States
Bernadette P.
The price is ￥28,046
￥53,175 total
includes taxes & fees
Dec 15 - Dec 16
Charming Cottage in the Heart of Catskill & Pet Friendly
Desk, iron/ironing board, WiFi, bed sheets
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥22,437
￥28,620 total
includes taxes & fees
Dec 19 - Dec 20
The Brooks Motel: Exceptional Suite
Dining
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

Pet-Friendly Hudson Escape w/ Hot Tub
2.0 star property
The price is ￥21,813
￥47,921 total
includes taxes & fees
Dec 15 - Dec 16
Pet-Friendly Hudson Escape w/ Hot Tub
Interior
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is ￥21,034
￥57,587 total
includes taxes & fees
Dec 17 - Dec 18
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Beach nearby
1 Bedroom | Cozy Lounge | Spacious

Vacation Home in Catskill

1 Bedroom | Cozy Lounge | Spacious
2.0 star property
1 Bedroom | Cozy Lounge | Spacious
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

Charming 3-bedroom Cabin for nature lovers
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is ￥24,151
￥49,810 total
includes taxes & fees
Dec 21 - Dec 22
Charming 3-bedroom Cabin for nature lovers
Dining
Sugar Shack - 300 square feet of pure sweetness.

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
10.0 out of 10, Exceptional, (3)
"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 ￥35,057
￥58,332 total
includes taxes & fees
Dec 16 - Dec 17
Sugar Shack - 300 square feet of pure sweetness.
Interior
Sweet Cozy Victorian in Housatonic. Close to everything.

Vacation Home in Housatonic

Sweet Cozy Victorian in Housatonic. Close to everything.
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ￥21,034
￥37,766 total
includes taxes & fees
Dec 15 - Dec 16
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ￥63,882
￥111,385 total
includes taxes & fees
Dec 18 - Dec 19
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥30,695
￥70,660 total
includes taxes & fees
Dec 15 - Dec 16
Cheerful 3-bedroom cottage with woodstove
3 bedrooms, iron/ironing board, WiFi, bed sheets
Tranquil Victorian on Charming Street

Vacation Home in Hudson

Tranquil Victorian on Charming Street
8.0 out of 10, Very Good, (2)
"What a darling house! We stayed with my mother and my adult kids for Thanksgiving and it was the perfect spot! The host was most attentive to all of our questions and request ex! It’s the perfect location for visiting the Hudson Valley and the house was so comfortable and accommodating for all of us! We loved everything about it!"
United States
Mary R.
The price is ￥38,797
￥88,999 total
includes taxes & fees
Dec 19 - Dec 20
Tranquil Victorian on Charming Street
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Vacation Home in Stottville

Hudson Hot Tub & Pet Escape
2.0 star property
The price is ￥19,632
￥44,169 total
includes taxes & fees
Dec 15 - Dec 16
Hudson Hot Tub & Pet Escape
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (6)
"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 ￥31,162
￥53,237 total
includes taxes & fees
Dec 16 - Dec 17
BLUSH: Boutique TINY home*private spa*walk to town
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

Mobile Home in Chatham

HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is ￥35,057
￥63,957 total
includes taxes & fees
Dec 21 - Dec 22
HunnyHAUS: Deluxe TINY*private spa*walk to town
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room was fantastic, cozy as can be! Also, as soon as you walk into the lobby it looked wonderful! The Manager, Jennifer was so nice to talk too! She made sure everything with room, etc. was good! She was a delight!"
Mary 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

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
  • Use the map to find apartments and other holiday homes in the Spencertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Spencertown while they last

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?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental near Spencertown is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like 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 Berkshire Botanical Garden. Norman Rockwell Museum and Catamount Aerial Adventure Park 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.