
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.

The Wylie Inn and Conference Center at Endicott College
$1,057
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Common and Salem Witch Museum are located nearby.
Enjoyed the hotel and the staff were excellent. I rated it slightly lower for two reasons. The first was we had a queen sized bed and looking at the bed, it was pretty small. It did not fill the bed frame, so we had to get an air mattress because we couldn’t both fit in the bed. The second was very minor and that was parking. The hotel shares the lot with the conference center, so if there is a conference, there is no parking except across the street. It happened twice to us and when we were leaving a conference attendee stopped us so she could get our spot.
It was a great hotel otherwise. It was great.
Reviewed on Aug 20, 2026

Boston Harbor Hotel
North End
$2,069
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Arrived late and not many food options. Room service was delayed. But otherwise a beautiful place!
Reviewed on Aug 19, 2026

Raffles Boston
Back Bay
$2,618
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

The Inn at Hastings Park, Relais & Chateaux - Boston
$1,506
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Burlington Mall and Minute Man National Historical Park are located nearby.

Arcadian Hotel
Coolidge Corner
$1,058
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
Me encanto el hotel, las camas muy cómodas el personal muy atento, me volvería alojar en el arcadian
Reviewed on Aug 21, 2026

Eurostars The Boxer
West End
$1,533
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Faneuil Hall Marketplace are located nearby.
Top Hotel Deals

Best Western Plus Landmark Inn
480 Main Street Laconia NH
Book a stay at this business-friendly hotel in Laconia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

Winnisquam Lake Inn
788 Laconia Rd Tilton NH
Stay at this hotel in Tilton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...

The Naswa Resort
1086 Weirs Blvd Laconia NH
Book a stay at this beach resort in Laconia. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our ...

The Centennial
96 Pleasant St Concord NH
Book a stay at this business-friendly hotel in Concord. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
76 Mountain Rd Epsom NH
Stay at this cabin in Epsom. Enjoy free parking, patios, and climate control. Popular attractions James Park and Epsom Public Library are located nearby.

Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
Book a stay at this spa hotel in Sanbornton. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff in our reviews. Popular attractions ...

Hampton Inn by Hilton Concord/Bow
515 South St Bow NH
Book a stay at this business-friendly hotel in Bow. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and ...

The Lake Estate on Winnisquam
725 Laconia Road Tilton NH
Book a stay at this luxury hotel in Tilton. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Lake Winnisquam and Silver Lake are located ...

Fireside Inn & Suites Gilford
17 Harris Shore Road Gilford NH
Book a stay at this business-friendly hotel in Gilford. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...

Quality Inn Loudon-Concord
2 Staniels Road Loudon NH
Book a stay at this business-friendly hotel in Loudon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...

DoubleTree by Hilton Downtown Concord
172 N Main St Concord NH
Book a stay at this business-friendly hotel in Concord. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...

The Wolfeboro Inn
90 N Main St Wolfeboro NH
Book a stay at this beach hotel in Wolfeboro. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular ...

Homewood Suites by Hilton Dover
21 Members Way Dover NH
Stay at this hotel in Dover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Dover ...

Super 8 by Wyndham Tilton/Lake Winnipesaukee
7 Tilton Rd Tilton NH
Book a stay at this business-friendly motel in Tilton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...

Holiday Inn Express & Suites Rochester by IHG
77 Farmington Rd Rochester NH
Book a stay at this business-friendly hotel in Rochester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.

Thu, Sep 10 - Sun, Sep 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$205
Roundtrip
found 2 hours ago

Thu, Nov 5 - Tue, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$267
Roundtrip
found 1 day ago

Thu, Nov 5 - Tue, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$277
Roundtrip
found 1 day ago

Thu, Nov 5 - Tue, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$277
Roundtrip
found 1 day ago
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations