Title: Book the Best Hotels with POOL in Ashley Falls in 2025 | Expedia.ca

 

[Ashley Falls Travel Guide](https://expedia.ca/Ashley-Falls.dx901768766462177280)[Hotels in Ashley Falls](https://expedia.ca/Ashley-Falls-Hotels.d901768766462177280.Travel-Guide-Hotels)[Vacation Rentals in Ashley Falls](https://expedia.ca/Ashley-Falls-Vacation-Rentals.d901768766462177280.Travel-Guide-VacationRentals)[Ashley Falls Car Rentals](https://expedia.ca/Car-Rentals-In-Ashley-Falls.d901768766462177280.Car-Rental-Guide)[Ashley Falls Vacation Packages](https://expedia.ca/Ashley-Falls.d901768766462177280.Destination-Travel-Guides)

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# Find Hotels with a Pool in Ashley Falls, MA from CA $135

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## Check availability on Ashley Falls Hotels with a Pool

Tonight

[Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=901768766462177280&startDate=2025-11-09&endDate=2025-11-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Nov 10 - Nov 11](https://www.expedia.ca/Hotel-Search?regionId=901768766462177280&startDate=2025-11-10&endDate=2025-11-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=901768766462177280&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=901768766462177280&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Ashley Falls Hotels with a Pool

![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/62ab3ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/11bb9318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

8.8/10

Excellent

(691)

"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "

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

Jamie

CA $143

CA $160 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/a2e409f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/be4af91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/549437da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Prospect Berkshires

Egremont

9.4/10

Exceptional

(13)

"Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway "

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

Andy

CA $358

CA $447 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information)

![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

9.0/10

Wonderful

(780)

"Place was great!"

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

Benjamin

CA $188

CA $230 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Ponds at Foxhollow

Lenox

8.6/10

Excellent

(132)

"Perfect location "

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

krystle

[](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

Stockbridge

8.8/10

Excellent

(1002)

"I love the ambience - historic and comfortable and excellent food. "

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

Nancy

CA $197

CA $283 total

includes taxes & fees

Nov 16 - Nov 17

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

![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/40c2786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/fd22ffcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/417c3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/18000000/17280000/17278300/17278254/282b9f8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cornwall Inn and Lodge

Cornwall Bridge

9.2/10

Wonderful

(153)

"This inn was very quaint and welcoming. It was a nice inn for the value. "

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

Jacqueline

CA $279

CA $321 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Torrington-Hotels-Cornwall-Inn-And-Lodge.h17278254.Hotel-Information)

![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ebf28595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/c97f0de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Little Lion

Great Barrington

8.6/10

Excellent

(543)

"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "

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

Maria

CA $181

CA $202 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/219cd416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/483e190d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunset Inn

Lee

7.6/10

Good

(409)

"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "

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

Kimberly

CA $120

CA $135 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

9.4/10

Exceptional

(751)

"We had a nice stay at the Fairfield Inn in Great Barrington. It’s conveniently located not far from downtown and just a short drive to Stockbridge. The front desk staff was welcoming, the room spacious and clean, and plenty of breakfast items to choose from. Definitely recommend!"

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

Denise

CA $201

CA $224 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/71ad964e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/e3b4fb9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/w1127h1499x0y0-42ebd11e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/95000000/94740000/94739600/94739508/d3489cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Little Cat Lodge

Copake Falls

9.4/10

Exceptional

(63)

"Wonderful stay! Very cute property, would visit again."

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

Arnav

[](https://www.expedia.ca/Hillsdale-Hotels-Little-Cat-Lodge.h94739508.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=2025-11-23&endDate=2025-11-24&regionId=901768766462177280&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true)

## Top Ashley Falls Hotel Reviews

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

### Quality Inn

10/10 Excellent

"The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. "

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

"I love the ambience - historic and comfortable and excellent food. "

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

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"I had a smooth check in. A little later I went back to the front desk to get an extra key, was asked my room number and last name. The associate, knew that I had asked for extra pillows when I made the reservation. I don't think he was even on my reservation on the computer yet to see the note. Asked if I had the extra pillows in the room and were they ok! Often hotels don't even notice this request, never mind remember it or ask about it. Great attention to details!"

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](//images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg)

### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"The staff was welcoming and friendly and our room was excellent"

[](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Clean and friendly "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![Monument Mountain Motel](//images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg)

### Monument Mountain Motel

10/10 Excellent

"Yes"

[](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![The Ponds at Foxhollow](//images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4_y.jpg)

### The Ponds at Foxhollow

10/10 Excellent

"All as promised!"

[](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information)

![Americas Best Value Inn Torrington CT](//images.trvl-media.com/lodging/1000000/10000/5800/5738/a9b48332_y.jpg)

### Americas Best Value Inn Torrington CT

10/10 Excellent

"Excellent parking."

[](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information)

![Interlaken Inn & Resort](//images.trvl-media.com/lodging/20000000/19680000/19679700/19679605/dbbfdf3a_y.jpg)

### Interlaken Inn & Resort

10/10 Excellent

"Super friendly and pet friendly. We are so grateful to have been able to check in early to finish getting ready for the wedding we attended! Thank you for the hospitality! "

[](https://expedia.ca/Torrington-Hotels-Interlaken-Inn-Resort.h19679605.Hotel-Information)

## Frequently asked questions

### What are some hotels with pools in Ashley Falls?

> [The Blue Elm - A Historic Berkshire Cottage](https://www.expedia.ca/Sheffield-Hotels-The-Blue-Elm-A-Historic-Berkshire-Cottage.h101469345.Hotel-Information): Features 3 restaurants, an outdoor pool, and spa services. [Quality Inn](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information): Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. [The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information): Features buffet, an indoor pool, and complimentary wired internet access. [The Red Lion Inn](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information): Offers full, an indoor pool, and complimentary wired internet access. [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information): Features cooked-to-order, a seasonal outdoor pool, and free self parking.

### What is there to see and do in Ashley Falls?

> The picturesque setting of Housatonic River showcases the area's natural beauty. Discover sights such as Ashley Falls Woods and Bartholomew's Cobble during your stay.

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-   [Flights to Great Barrington](https://www.expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights)
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-   [Great Barrington Vacation Rentals](https://www.expedia.ca/Great-Barrington-Vacation-Rentals.d110336.Travel-Guide-VacationRentals)
-   [Mount Washington Vacation Rentals](https://www.expedia.ca/Mount-Washington-Vacation-Rentals.d553248634999242901.Travel-Guide-VacationRentals)

-   [Book Hotels with a Pool in Ashley Falls on Expedia.com](https://www.expedia.com/Ashley-Falls-Hotels-Hotel-With-Pool.0-0-d901768766462177280-tHotelwithPool.Travel-Guide-Filter-Hotels)