Deals on vacations and trips to Ashuwillticook Rail Trail

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Ashuwillticook Rail Trail flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,073, price is now $918 per person
$918
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

3 out of 5
Save 100% on your flight
Price was $12,297, price is now $9,587 per person
$9,587
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. An outdoor pool and a terrace are also provided.
Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

3 out of 5
Save 100% on your flight
Price was $2,329, price is now $1,906 per person
$1,906
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,126, price is now $984 per person
$984
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A 24-hour gym and barbecue grills are also provided.
Perfect Family Vacation Home in the Mountains

Perfect Family Vacation Home in the Mountains

2 out of 5
Save 100% on your flight
Price was $2,066, price is now $1,815 per person
$1,815
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Top Ashuwillticook Rail Trail hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$92 nightly
The price is $103 total per night
$103 total
May 7 - May 8
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $107 total per night
$107 total
May 7 - May 8
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $208 total per night
$208 total
May 17 - May 18
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Spa
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

3.5 out of 5
190 Meadow Street South Lee MA
Free Cancellation
$145 nightly
The price is $162 total per night
$162 total
May 10 - May 11
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
$144 nightly
The price is $160 total per night
$160 total
May 27 - May 28
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-out. Enjoy the hot tub and perks like free self parking.
Pool
Hot Tub
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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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