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

Spencertown Holiday Rentals

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Check prices for these dates

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

Our top choices for Spencertown holiday rentals

Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (159 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 HK$1,087
HK$1,217 total
includes taxes & fees
4 Aug - 5 Aug
Micosta Leisure Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,029 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$943
HK$1,228 total
includes taxes & fees
27 Aug - 28 Aug
Berkshire Mountain Lodge
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is HK$769
HK$1,037 total
includes taxes & fees
29 Jul - 30 Jul
All comforts of home
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, (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 HK$1,804
HK$2,977 total
includes taxes & fees
29 Jul - 30 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is HK$833
HK$1,108 total
includes taxes & fees
3 Aug - 4 Aug
All the comforts of home
Coffee/tea maker, fridge, microwave, oven

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.
The price is HK$812
HK$1,213 total
includes taxes & fees
9 Aug - 10 Aug
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is HK$549
HK$1,614 total
includes taxes & fees
29 Jul - 30 Jul
NEW RENO - Chalet-style farm loft near Tanglewood
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,176
HK$1,493 total
includes taxes & fees
29 Jul - 30 Jul
The Brooks Motel: Exceptional Suite
Terrace/patio

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)
The price is HK$2,078
HK$2,574 total
includes taxes & fees
19 Aug - 20 Aug
BLUSH: Boutique TINY home*private spa*walk to town
Dining

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 HK$2,157
HK$2,742 total
includes taxes & fees
3 Aug - 4 Aug
Sugar Shack - 300 square feet of pure sweetness.
Exterior

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 HK$2,435
HK$4,466 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
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 HK$1,466
HK$2,846 total
includes taxes & fees
4 Aug - 5 Aug
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Interior

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 HK$1,786
HK$2,722 total
includes taxes & fees
27 Aug - 28 Aug
Cozy Riverside Berkshires Retreat
Dining

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is HK$1,466
HK$2,872 total
includes taxes & fees
6 Aug - 7 Aug
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Exterior detail

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 HK$2,282
HK$5,112 total
includes taxes & fees
19 Aug - 20 Aug
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Pool

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 HK$1,772
HK$3,232 total
includes taxes & fees
29 Jul - 30 Jul
Hudson NY’S Country Serenity Guest Suite.
Coffee/tea maker, fridge, microwave, oven

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 HK$2,117
HK$3,188 total
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Desk, iron/ironing board, WiFi, bed sheets

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 HK$1,239
HK$1,563 total
includes taxes & fees
29 Jul - 30 Jul
The Brooks Motel: Exceptional Suite
Dining

Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.0 out of 10, Wonderful, (14 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
The price is HK$1,023
HK$2,042 total
includes taxes & fees
29 Jul - 30 Jul
Charming Yacht on Catskill Creek
TV, fireplace, DVD player, books

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 HK$1,482
HK$5,920 total
includes taxes & fees
21 Aug - 22 Aug
Mtn-View Retreat in Huson Valley: Great for Groups
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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Loved the voew from our balcony of the lake. Breakfasts were great. Well located. A good place to see the Berkshires from."
Judith 5-night trip
Posted 2 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Spencertown is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and 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. The Mac-Haydn Theatre and Berkshire Botanical Garden 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.