Ashuwillticook Rail Trail Holiday Rentals

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Holiday Rentals in Ashuwillticook Rail Trail

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2134)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is NZ$208
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (984)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
The price is NZ$286
includes taxes & fees
15 Nov - 16 Nov
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$373
includes taxes & fees
15 Dec - 16 Dec
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is NZ$325
includes taxes & fees
15 Nov - 16 Nov
Taborton Harvest Boulder Pines Cabin in the woods

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$526
includes taxes & fees
17 Nov - 18 Nov
Pet Friendly Riverfront Home in Great Barrington

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (228)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is NZ$1,303
includes taxes & fees
20 Nov - 21 Nov
Spacious 5-bedroom house in charming Lee with WiFi

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is NZ$570
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom Cabin for nature lovers

Bear Creek Cabin

Charlemont
10.0 out of 10, Exceptional, (42)
"We enjoyed our stay!!"
United States
Hillary S.
The price is NZ$1,063
includes taxes & fees
16 Nov - 17 Nov
Bear Creek Cabin

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is NZ$1,967
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Woodford
8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
United States
Elzbieta M.
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
The price is NZ$1,294
includes taxes & fees
15 Nov - 16 Nov
Comfortable Berkshires retreat on mtn resort, SISO

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lee
9.4 out of 10, Exceptional, (71)
"Liked the 3 room suite, and 100 year old oak interior and the front porch, esp. as time went on. Walk to many restaurants, some only open in Fall after Wednesday. Some of the old doors fit like old doors, not unexpected, and felt like home away from home as time went on. Liked Fridge, coffee maker and small kitchen that we hardly used, but would have used more if longer stay."
United States
Leonard
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Pownal
9.4 out of 10, Exceptional, (84)
"Great communication from the hosts and convenient to Williamstown, Bennington and all things VT. Clean and comfortable. Look forward to coming back!"
United States
Emily N.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
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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Find out more about Ashuwillticook Rail Trail

Everything you need to know about Ashuwillticook Rail Trail holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashuwillticook Rail Trail holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashuwillticook Rail Trail holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashuwillticook Rail Trail holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashuwillticook Rail Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashuwillticook Rail Trail holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashuwillticook Rail Trail holiday rentals we have selected for you start as low as NZ$208 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashuwillticook Rail Trail rentals

At Expedia, we put the best Ashuwillticook Rail Trail holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashuwillticook Rail Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashuwillticook Rail Trail holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashuwillticook Rail Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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