Search Vacation Homes in Ashuwillticook Rail Trail

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 329 Vacation Homes in Ashuwillticook Rail Trail with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (244)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is SAR 563
SAR 859 total
includes taxes & fees
4 May - 5 May
Berkshire Village Carriage House - Super Private!!
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is SAR 2,059
SAR 3,890 total
includes taxes & fees
5 May - 6 May
Hancock Village Inn at Jiminy Peak
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Property grounds

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (72)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "
Peace and quiet on the lake
Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Such a large house with so many areas for activities. Close to a lot of fun things to do like axe throwing, an escape room, distilleries, breweries, etc."
GAMERS HAVEN, River Wine Inn!
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (71)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home
A heated pool

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Bright three-level home with water views, jetted tub, firepit, and pool table
Fridge, microwave, oven, stovetop

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (27)
"Awesome Cabin, private and peaceful location."
Bright three-level home with water views, jetted tub, firepit, and pool table
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Exterior

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (121)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
Fridge, microwave, stovetop, dishwasher

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

9.6 out of 10, Exceptional, (5)
"We usually don’t book places that don’t have several reviews, but since we knew the area, we decided to “take a chance”. We are very glad we did! We stayed 5 nights and were very happy. The heat pumps were great since the temperature dipped below 0. The accommodations were very comfortable and we had everything we needed to make our stay enjoyable. "
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
Lakeside 5-BR Home in Idyllic Berkshires
TV, fireplace, offices

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (2)
"Celebrated a birthday with a group of old friends. Great location near Lee. Enjoyed the lake views. Fires inside and outside. Home is well decorated and clean."
Lakeside 5-BR Home in Idyllic Berkshires
2.5mi from the lake! Fire pit, arcade, yard games!
Fridge, microwave, oven, stovetop

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is SAR 739
SAR 1,873 total
includes taxes & fees
6 May - 7 May
2.5mi from the lake! Fire pit, arcade, yard games!
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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Other property types in Ashuwillticook Rail Trail

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1802)
"The property was clean and the staff very accommodated."
The price is SAR 426
SAR 517 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is SAR 503
SAR 562 total
includes taxes & fees
4 May - 5 May
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (14)
"Near Jacob's Pillow!"
Pristine Home In Becket Woods
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.