Spencertown Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Spencertown vacation rentals

Property grounds

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, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is ￥36,874
￥60,871 total
includes taxes & fees
Jun 23 - Jun 24
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ￥51,142
￥100,488 total
includes taxes & fees
Jun 22 - Jun 23
Treetop Hideaway in Tyringham
Pool

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (6 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is ￥41,707
￥90,189 total
includes taxes & fees
Jun 21 - Jun 22
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is ￥33,205
￥74,379 total
includes taxes & fees
Jul 7 - Jul 8
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (154 reviews)
"The room was cozy. In a very quiet part of town. The check in process was easy. I would definitely stay again while in town."
United States
Kathleen
The price is ￥20,844
￥23,346 total
includes taxes & fees
Jun 30 - Jul 1
Micosta Leisure Inn
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,736
￥21,216 total
includes taxes & fees
Jun 28 - Jun 29
All comforts of home
Dining

Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.0 out of 10, Wonderful, (12 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
The price is ￥20,922
￥41,568 total
includes taxes & fees
Jun 21 - Jun 22
Charming Yacht on Catskill Creek
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
The price is ￥28,874
￥56,234 total
includes taxes & fees
Jun 18 - Jun 19
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.6 out of 10, Exceptional, (39 reviews)
"We Absolutely loved our weekend stay here! Beautiful property and just as described!!! Will definitely be back!!!"
United States
Jessica R.
The price is ￥25,986
￥57,670 total
includes taxes & fees
Jun 22 - Jun 23
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is ￥17,026
￥22,661 total
includes taxes & fees
Jun 30 - Jul 1
All the comforts of home
Outdoor dining

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is ￥33,205
￥62,162 total
includes taxes & fees
Jun 21 - Jun 22
Hudson NY’S Country Serenity Guest Suite.
Terrace/patio

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥29,980
￥57,638 total
includes taxes & fees
Jun 18 - Jun 19
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥31,423
￥88,758 total
includes taxes & fees
Jun 22 - Jun 23
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is ￥31,455
￥72,920 total
includes taxes & fees
Jun 22 - Jun 23
stylish Berkshires Retreat
Beach

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3 reviews)
"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 ￥17,645
￥37,430 total
includes taxes & fees
Jun 18 - Jun 19
Berkshires Apartment at the Stephentown Hotel
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
The price is ￥38,236
￥58,826 total
includes taxes & fees
Jun 23 - Jun 24
Home in Great Barrington
Dining

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is ￥29,980
￥58,177 total
includes taxes & fees
Jun 22 - Jun 23
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Interior

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is ￥23,950
￥81,051 total
includes taxes & fees
Jun 30 - Jul 1
Charles Cottage Near Warren St New Renovation
Fridge, microwave, stovetop, dishwasher

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥28,056
￥88,893 total
includes taxes & fees
Jun 21 - Jun 22
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is ￥23,099
￥60,186 total
includes taxes & fees
Jun 23 - Jun 24
Near Tanglewood: Historic Summer Retreat
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Simple comfort and convenience, combined with super friendly guest services, make this my go to for the one or two night stays when . I come back to where I grew up to visit old friends and family !"
christopher 1-night trip
Posted 9 hours ago
Quality Inn Great Barrington

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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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?

Cozy Riverside Berkshires Retreat: This vacation home rental near Spencertown is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and an electric kettle, so you can cook with friends or family. 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 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.