Title: Spencertown Vacation Home Rentals from CA $198: Search Top Private Vacation Homes for Rent | Expedia.ca

  

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Photo by Charlie Rhodes

# Spencertown Vacation Rentals

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000449614&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000449614&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000449614&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000449614&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Spencertown Vacation Homes

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/4b325a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/f501a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-b25e9082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/60000000/60000000/59995300/59995220/90-00a818b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### All the comforts of home

Hudson

9.2/10

Wonderful

(26)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Marisa P.

CA $149

CA $198 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Hudson-Hotels-All-The-Comforts-Of-Home.h59995220.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/e0f691bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/dcb799f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Home in Great Barrington

Great Barrington

9.8/10

Exceptional

(24)

"Enjoyed our stay!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Fred W.

CA $210

CA $359 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/665b8282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/f26544ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/99d3f85f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books, computer monitors](https://images.trvl-media.com/lodging/76000000/75600000/75599900/75599864/af920cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cheerful 3-bedroom cottage with woodstove

Sheffield

10/10

Exceptional

(39)

"The property was centrally located for skiing, and was a comfortable stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly R.

CA $276

CA $634 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sheffield-Hotels-Cheerful-3-Bedroom-Cottage-With-Woodstove.h75599864.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/43b40eb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/10c07c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/06261f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99250000/99243600/99243554/8de4c71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Near Tanglewood: Historic Summer Retreat

New Lebanon

9.6/10

Exceptional

(22)

"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patty W.

CA $244

CA $587 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/New-Lebanon-Hotels-Near-Tanglewood-Historic-Summer-Retreat.h99243554.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/329257ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/04c3bec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/e73088a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111830000/111821600/111821595/a7b21f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bungalow in the Berkshires

Lee

10/10

Exceptional

(3)

"We had a lovely stay. Easy check in and communication was great. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dale G.

CA $421

CA $587 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Lee-Hotels-Bungalow-In-The-Berkshires.h111821595.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/a4dc2b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/d3c8327e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/32714507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109600000/109590900/109590815/25e02c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9.4/10

Exceptional

(3)

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah D.

CA $266

CA $658 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Sun-Filled-Lenox-Retreat-Minutes-To-Tanglewood.h109590815.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/a38bbe4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

7.8/10

Good

(6)

"Very clean and spacious! We enjoyed our stay with our small pup!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann C.

CA $377

CA $680 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/c0195267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/62efe3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/4c35929b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658957/c605aa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hudson Hot Tub & Pet Escape

Stottville

CA $189

CA $423 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hudson-Hotels-Hudson-Hot-Tub-Pet-Escape.h120658957.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/505c31c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player, books, stereo](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/8d87241a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/53261c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29620000/29615600/29615546/64f95c5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Barrington Get Away

Great Barrington

9.4/10

Exceptional

(23)

"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amy B.

CA $358

CA $675 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Great-Barrington-Hotels-Great-Barrington-Get-Away.h29615546.Hotel-Information)

![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, paper towels](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/c57b8d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Great Barrington

9.0/10

Wonderful

(2)

"Close to a great bakery and near to a farm market and shopping mall. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cristine C.

CA $268

CA $342 total

includes taxes & fees

Nov 6 - Nov 7

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/e3e0e9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/8e812ffc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/094a3cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32810000/32807400/32807378/52f8efbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie

10/10

Exceptional

(54)

"Great spot on the lake. Super quiet and relaxing."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

vincent m.

CA $379

CA $740 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Albany-Hotels-Escape-To-Lakefront-Leisurehudson.h32807378.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/2d6b60e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/77b3a9cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/52a28496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120280000/120277100/120277085/c26c1c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Hudson

10/10

Exceptional

(1)

"Perfect Hudson Valley Girls weekend! The house was gorgeous, so incredibly clean, comfortable beds, beautiful outdoor fire pit area with jacuzzi overlooking the river. All the little efforts were put into the property to make it feel like an intimate home, like providing plenty of additional towels for the jacuzzi, shampoo / conditioner in the showers and more. We were able to spend each day in Hudson downtown enjoying all the boutiques and restaurants because it was such an easy drive into...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Caitlin W.

CA $411

CA $857 total

includes taxes & fees

Oct 23 - Oct 24

[](https://www.expedia.ca/Hudson-Hotels-3BR-Creekside-Retreat-With-Hot-Tub.h120277085.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/4d036f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/e6b4678e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/725d323d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92460000/92452800/92452756/ec6797eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy. Clean. Free bagel shop.

Great Barrington

10/10

Exceptional

(10)

"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carly F.

CA $561

CA $930 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Clean-Free-Bagel-Shop.h92452756.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/aaef5562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/19823f49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/a9d8787c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23280000/23274600/23274540/e73723b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Hudson

9.6/10

Exceptional

(25)

"We loved our stay and this house made our trip. The bathroom and kitchen were especially memorable but we loved all the little details that added up to one stunningly restored historic home."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah P.

CA $841

CA $1,530 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Hudson-Hotels-Light-Filled-Hudson-Home-With-Designer-Sauna.h23274540.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/w906h683x60y0-974ef863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/dc67334d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/w904h683x60y0-5201af76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103620000/103611900/103611832/909d9f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed

Hudson

CA $295

CA $544 total

includes taxes & fees

Oct 22 - Oct 23

[](https://www.expedia.ca/Hudson-Hotels-1BR-Hudson-Apartment.h103611832.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/772f14ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, printers](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/6ef7616b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/61aeb8a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/121000000/120150000/120149100/120149051/ee5ac04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

10/10

Exceptional

(1)

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Roberta

CA $882

CA $1,972 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Great-Barrington-Hotels-Berkshires-Best-Large-Deck-With-Hotub.h120149051.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/fc7a38f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/c49add02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/223b97ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/100000000/99770000/99761000/99760997/6ae561f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tranquil Victorian on Charming Street

Hudson

6.0/10

(1)

"Interior has been recently upgraded and is nicely done providing a pleasant stay. Host needs to be more responsive as we had an hours delay in accessing the property. Host did not respond to messages over a 6 hour period prior to arrival."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jim & Linda

CA $349

CA $802 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Hudson-Hotels-Tranquil-Victorian-On-Charming-Street.h99760997.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/c189cee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hancock Village Inn at Jiminy Peak

Hancock

10/10

Exceptional

(15)

"Amazing Inn. Cozy and everything we needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Price F.

CA $770

CA $1,468 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103590000/103585300/103585202/8abb6d32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, stereo](https://images.trvl-media.com/lodging/104000000/103590000/103585300/103585202/af1c5a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/104000000/103590000/103585300/103585202/6a496ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103590000/103585300/103585202/a2566335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Estate: Heated Pool, Tennis, Sauna, Hot Tub

Catskill

CA $1,192

CA $2,033 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/Catskill-Hotels-Serene-Estate-Heated-Saltwater-Pool.h103585202.Hotel-Information)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/537c5cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/5c7aed99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/5dbea083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121090000/121082600/121082559/485974a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artists’ Hideaway in Old Chatham

Old Chatham

CA $282

CA $621 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Old-Chatham-Hotels-Artists-Hideaway-In-Old-Chatham.h121082559.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-03&endDate=2025-11-04&regionId=3000449614&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg)

Save an average of 15% on thousands of hotels when you're signed in

[Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSpencertown-Private-Vacation-Homes.d3000449614-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSpencertown-Private-Vacation-Homes.d3000449614-aaPrivateVacationHomes.Travel-Guide-Accommodation)

## Top Spencertown Hotel Reviews

![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Kitchen and parking both very good"

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

10/10 Excellent

"In a very nice annex suite."

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg)

### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

"Nice clean and new. I had a nice stay, with restaurants across the street and a dunkin very close for the morning "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Enjoyable stay. Staff were very nice. "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg)

### Quality Inn

10/10 Excellent

"Clean room, nice location "

[](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![St. Charles Hotel](//images.trvl-media.com/lodging/2000000/1640000/1639400/1639318/d1c362b4_y.jpg)

### St. Charles Hotel

10/10 Excellent

"Rooms clean minimal and comfortable bed"

[](https://expedia.ca/Hudson-Hotels-St-Charles-Hotel.h1639318.Hotel-Information)

![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"Yes"

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Great stay-- would stay here again-- safe, nice welcome from Cameron at front desk, room was clean and cozy. Bed was very comfortable. Didn't have breakfast. I usually stay in Pittsfield at a hotel that has given me a discount since March when my mother was put into a nursing home. I normally try to come down twice a month from CNY--needless to say it is expensive for me.. Random question-- do you offer discounts?"

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![voco James Newbury Hudson Valley by IHG](//images.trvl-media.com/lodging/95000000/94300000/94292700/94292624/d7f7134f_y.jpg)

### voco James Newbury Hudson Valley by IHG

10/10 Excellent

"Our visit started with Christy at the front desk. We had arrived prior to check-in time. She found a room for us and quickly had us on our way to our beautiful room. The rooms are spacious, luxurious, quiet and well appointed. Breakfast was delicious; service was warm and friendly. I would highly recommend this hotel. "

[](https://expedia.ca/Coxsackie-Hotels-James-Newbury-Hotel.h94292624.Hotel-Information)

## Find out more about Spencertown

## Spencertown Vacation Homes information

| Number of reviews | 235 |
| --- | --- |
| Accommodation | 471 Vacation Homes |
| Lowest Price | CA $198 |
| Highest Price | CA $2,041 |

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-   [Visit Stottville](https://www.expedia.ca/Stottville.dx3000351293)

-   [Car rental Chatham](https://www.expedia.ca/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)
-   [Hertz Rental Cars in Chatham](https://www.expedia.ca/Hertz-Car-Rentals-In-Chatham.d6046736-c40.Car-Rental-Guide-Suppliers)

-   [Chatham Vacation Rentals](https://www.expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)

-   [Book Vacation Homes in Spencertown on Expedia.com](https://www.expedia.com/Spencertown-Private-Vacation-Homes.d3000449614-aaPrivateVacationHomes.Travel-Guide-Accommodation)