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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (175 reviews)
"Great little place."
United States
Kim
The price is ￥19,994
￥22,394 total
includes taxes & fees
Oct 13 - Oct 14
Micosta Leisure Inn
Lobby

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,143 reviews)
"Clean & comfortable stay"
United States
Robert
The price is ￥12,348
￥17,259 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (13 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,026
￥52,992 total
includes taxes & fees
Sep 20 - Sep 21
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 ￥38,914
￥49,525 total
includes taxes & fees
Sep 22 - Sep 23
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

5. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (59 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,331
￥20,670 total
includes taxes & fees
Sep 27 - Sep 28
All comforts of home
Dining

6. 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 ￥38,627
￥49,160 total
includes taxes & fees
Sep 22 - Sep 23
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

7. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is ￥31,026
￥58,900 total
includes taxes & fees
Sep 30 - Oct 1
Ideal location for summer and winter activities with plenty of outdoor space.
Private kitchen

8. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥10,859
￥31,919 total
includes taxes & fees
Sep 20 - Sep 21
NEW RENO - Chalet-style farm loft near Tanglewood
Private kitchen

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.6 out of 10, Exceptional, (4 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is ￥17,452
￥24,172 total
includes taxes & fees
Sep 28 - Sep 29
Cozy 1-bedroom studio in serene Great Barrington with AC
Property grounds

10. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥16,597
￥22,090 total
includes taxes & fees
Sep 21 - Sep 22
All the comforts of home
Interior

11. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
Luxury Barn Retreat — All-Season Escape Awaits!
Pool

12. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is ￥30,871
￥56,815 total
includes taxes & fees
Sep 23 - Sep 24
Hudson NY’S Country Serenity Guest Suite.
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 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 ￥27,349
￥49,752 total
includes taxes & fees
Sep 25 - Sep 26
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

14. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (25 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥29,669
￥46,657 total
includes taxes & fees
Sep 30 - Oct 1
Riverside Retreat in the Berkshires
Terrace/patio

15. 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 ￥29,009
￥56,641 total
includes taxes & fees
Sep 21 - Sep 22
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Private kitchen

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥34,485
￥51,517 total
includes taxes & fees
Sep 28 - Sep 29
Home in Great Barrington
Exterior detail

17. 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, (5 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 ￥32,663
￥85,767 total
includes taxes & fees
Sep 21 - Sep 22
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Beach

18. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is ￥29,180
￥46,803 total
includes taxes & fees
Sep 30 - Oct 1
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Living area

19. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is ￥16,409
￥38,501 total
includes taxes & fees
Sep 20 - Sep 21
1800s Carriage house in Berkshires / Hudson Valley
Exterior

20. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (133 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 ￥64,075
￥118,498 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
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
"Liked everything! Mostly, the people. The staff was friendly and excited to serve us"
John 1-night trip
Posted 17 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:

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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?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near Spencertown offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Art Omi International Arts Center - Fields Sculpture Park. Berkshire Botanical Garden and Norman Rockwell Museum 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.