Photo by Charlie Rhodes

Spencertown Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Spencertown

Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is HK$966
HK$1,080 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

3.0 star property
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is HK$1,011
HK$1,132 total
includes taxes & fees
30 Nov - 1 Dec
Micosta Leisure Inn
Property grounds
All comforts of home

Apartment in Hudson

9.8 out of 10, Exceptional, (51)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$763
HK$1,029 total
includes taxes & fees
4 Dec - 5 Dec
All comforts of home
Property grounds
All the comforts of home

Holiday Home in Hudson

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 HK$826
HK$1,099 total
includes taxes & fees
7 Dec - 8 Dec
All the comforts of home
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

9.8 out of 10, Exceptional, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is HK$1,169
HK$2,556 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

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 HK$824
HK$1,766 total
includes taxes & fees
30 Nov - 1 Dec
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop
Home in Great Barrington

Holiday Home in Great Barrington

9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
The price is HK$1,267
HK$2,119 total
includes taxes & fees
2 Dec - 3 Dec
Home in Great Barrington
Terrace/patio
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

2.0 star property
The price is HK$1,244
HK$2,574 total
includes taxes & fees
2 Dec - 3 Dec
Pet-Friendly Hudson Escape w/ Hot Tub
Interior
Charming 3-bedroom Cabin for nature lovers

Cabin in Stephentown

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 HK$1,206
HK$2,486 total
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom Cabin for nature lovers
Dining
Guesthouse Cabin vacation rentals in Berkshire County

Cabin in Sheffield

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 HK$3,189
HK$5,560 total
includes taxes & fees
3 Dec - 4 Dec
Guesthouse Cabin vacation rentals in Berkshire County
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Holiday Home in Housatonic

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 HK$1,050
HK$1,885 total
includes taxes & fees
4 Dec - 5 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Mobile Home in Chatham

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.
Sugar Shack - 300 square feet of pure sweetness.
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

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 HK$1,159
HK$1,472 total
includes taxes & fees
1 Dec - 2 Dec
The Brooks Motel: Exceptional Suite
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Holiday Home in Hillsdale

8.4 out of 10, Very good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
The price is HK$1,493
HK$4,129 total
includes taxes & fees
6 Dec - 7 Dec
Perfect House In Hillsdale, Brings Friends & Fam
Exterior
Berkshires farm, 30+ guests, 50 acres

Cottage in New Lebanon

2.0 star property
The price is HK$6,301
HK$12,804 total
includes taxes & fees
2 Dec - 3 Dec
Berkshires farm, 30+ guests, 50 acres
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Holiday Home in Pittsfield

2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is HK$2,093
HK$3,832 total
includes taxes & fees
2 Dec - 3 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

Mobile Home in Chatham

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 HK$2,450
HK$3,807 total
includes taxes & fees
12 Dec - 13 Dec
BLUSH: Boutique TINY home*private spa*walk to town
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Holiday Home in Stottville

2.0 star property
The price is HK$1,120
HK$2,380 total
includes taxes & fees
3 Dec - 4 Dec
Hudson Hot Tub & Pet Escape
Games room
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is HK$1,575
HK$2,315 total
includes taxes & fees
30 Nov - 1 Dec
Pet Friendly Riverfront Home in Great Barrington
Property grounds
Cheerful 3-bedroom cottage with woodstove

Holiday Home in Sheffield

10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,843
HK$3,909 total
includes taxes & fees
8 Dec - 9 Dec
Cheerful 3-bedroom cottage with woodstove
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

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!

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Frequently asked questions

Can I find a holiday rental in Spencertown?

Yes, there are holiday rentals close to the most popular sights in Spencertown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Spencertown has to offer?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of 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 holiday with amenities such as a selection of games.

How many holiday rentals will I find in Spencertown?

Expedia has 3 holiday 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. Berkshire Botanical Garden and Norman Rockwell Museum are a couple of places you'll find in the wider area.

What’s a holiday rental in Spencertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Spencertown. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.