Pittsfield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Pittsfield Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hinckleys Dreamwood Cottages
$1,656
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Bangor (BGR)
Stay at this cottage in Bar Harbor. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Acadia National Park's Visitors Center and Bar Harbor Whale Watch Co are located nearby.
Great location away from the crowds. Quiet at night.
Reviewed on Aug 11, 2026
Downtown Apartments in Bar Harbor
Downtown Bar Harbor
$2,321
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Bangor (BGR)
Stay at this apartment in Bar Harbor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Acadia National Park's Visitors Center and Acadia National Park are located nearby.
Perfect location and very nice, spacious property. We needed a last minute booking and this worked out perfectly.
Reviewed on Aug 8, 2026
3BedroomApt Pool CampFire PlayArea
$2,293
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Bangor (BGR)
Stay at this apartment in Bar Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Acadia National Park's Visitors Center and Garland Farm are located nearby.
Nice spot that is very close to bar harbor. Very clean and great for a large amount of people.
Reviewed on Jun 30, 2025
3Bedroom2Bath CarriageHouse Pet Friendly
$2,646
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Bangor (BGR)
Stay at this vacation home in Bar Harbor. Enjoy free WiFi, free parking, and a garden. Popular attractions Acadia National Park's Visitors Center and Garland Farm are located nearby.
The Pathmaker Hotel
$2,278
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Bangor (BGR)
Stay at this hotel in Bar Harbor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Acadia National Park's Visitors Center and Acadia National Park are located nearby.
Bar Harbor Main Street Apartments
Downtown Bar Harbor
$2,931
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Kansas City (MKC) to Bangor (BGR)
Stay at this apartment in Bar Harbor. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Acadia National Park's Visitors Center and Acadia National Park are located nearby.
Great location, plenty of space. Bathroom needs repair work but otherwise a great choice
Reviewed on Oct 15, 2025
Top Hotel Deals
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Stay at this hotel in Waterville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Elmwood
455 Kennedy Memorial Dr Waterville ME
Stay at this motel in Waterville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Plus Waterville Grand Hotel
375 Main Street Waterville ME
Book a stay at this business-friendly hotel in Waterville. Enjoy free parking, 2 restaurants, and a fitness center. Our guests praise the helpful staff in our ...
Holiday Inn Express & Suites Waterville - North by IHG
332 Main St Waterville ME
Book a stay at this business-friendly hotel in Waterville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Skowhegan By Kasa
7 Island Ave Skowhegan ME
Stay at this hotel in Skowhegan. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Margaret Chase Smith Library and Skowhegan ...
Lockwood Hotel
9 Main St Waterville ME
Book a stay at this business-friendly hotel in Waterville. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and ...
The Towne Motel
172 Madison Ave Skowhegan ME
Stay at this motel in Skowhegan. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Hampton Inn Waterville
425 Kennedy Memorial Dr Waterville ME
Book a stay at this business-friendly hotel in Waterville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Budget Host Airport Inn
400 Kennedy Memorial Dr Waterville ME
Stay at this motel in Waterville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Gordon Center For Creative & Performing Arts and Tree ...
Belmont Motel
273 Madison Ave Skowhegan ME
Book a stay at this ski motel in Skowhegan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Skowhegan State Fairgrounds and Margaret Chase ...
Canaan Motel
205 Main St Canaan ME
Stay at this motel in Canaan. Enjoy free WiFi, free parking, and air conditioning. Popular attraction Eaton Mountain is located nearby.
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Oct 20 - Wed, Nov 11
TPA
Tampa Intl.
BGR
Bangor Intl.
$209
Roundtrip
found 5 days ago
Tue, Oct 20 - Wed, Nov 11
TPA
Tampa Intl.
BGR
Bangor Intl.
$269
Roundtrip
found 5 days ago
Thu, Aug 27 - Mon, Aug 31
EWR
Newark Liberty Intl. Airport
BGR
Bangor Intl.
$289
Roundtrip
found 2 days ago
Wed, Sep 30 - Sat, Oct 17
TPA
Tampa Intl.
BGR
Bangor Intl.
$310
Roundtrip
found 23 hours ago
Thu, Oct 22 - Sun, Oct 25
JFK
John F. Kennedy Intl.
AUG
Augusta State
$438
Roundtrip
found 2 days ago
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