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Pittsfield Vacation Packages

Build your package with 2 more options

Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
American Inn and Suites Dundee

American Inn and Suites Dundee

2 out of 5
Price was $429, price is now $313 per person
$313
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
Book a stay at this business-friendly hotel in Dundee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Holiday Inn Dundee-Waterpark and Russell Stover Candies are located nearby.
Quite

Reviewed on Aug 12, 2026

Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $702, price is now $407 per person
$407
per person
Sep 18 - Sep 20
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
Book a stay at this boutique hotel in Plymouth. Enjoy free parking, 3 restaurants, and a golf course. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Laurel Park Place and St. John's Golf & Conference Center are located nearby.
Spacious clean rooms. Nice facility. Well maintained gardens. Courteous staff.

Reviewed on Aug 13, 2026

Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Save 100% on your flight
Price was $1,419, price is now $939 per person
$939
per person
Sep 24 - Sep 27
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
Book a stay at this boutique hotel in Ann Arbor. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Stadium and Briarwood Mall are located nearby.
Staff was GREAT

Reviewed on Aug 13, 2026

The Townsend Hotel

The Townsend Hotel

4 out of 5
Save 100% on your flight
Price was $657, price is now $439 per person
$439
per person
Sep 18 - Sep 20
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
Book a stay at this boutique hotel in Birmingham. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Detroit Zoo and Lyudviga Couture are located nearby.
Top-notch

Reviewed on Aug 9, 2026

Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Save 100% on your flight
Price was $770, price is now $554 per person
$554
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
Book a stay at this business-friendly hotel in Detroit. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Little Caesars Arena and Comerica Park are located nearby.

Daxton Hotel Birmingham, Curio Collection by Hilton

Daxton Hotel Birmingham, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $957, price is now $718 per person
$718
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
Stay at this hotel in Birmingham. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Detroit Zoo and Lyudviga Couture are located nearby.
Very clean! Awesome staff!! Shuttle Driver Andre was amazing and Nix at the front desk was a pleasure to work with! Will visit again!

Reviewed on Aug 10, 2026

Graduate by Hilton Ann Arbor

Graduate by Hilton Ann Arbor

4 out of 5
Save 100% on your flight
Price was $1,144, price is now $883 per person
$883
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
Book a stay at this business-friendly hotel in Ann Arbor. 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 Michigan Stadium and Briarwood Mall are located nearby.

Ann Arbor Marriott Ypsilanti at Eagle Crest

Ann Arbor Marriott Ypsilanti at Eagle Crest

4 out of 5
Price was $945, price is now $747 per person
$747
per person
Nov 5 - Nov 8
found 22 hours ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
Book a stay at this golf hotel in Ypsilanti. Enjoy free WiFi, a golf course, and breakfast (surcharge). Popular attractions Ford Lake and Riverside Arts Center are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Save 100% on your flight
Price was $888, price is now $596 per person
$596
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Detroit (DTW)
Saint John's Resort

Saint John's Resort

4 out of 5
Save 100% on your flight
Price was $1,725, price is now $958 per person
$958
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Detroit (DTW)
Weber's Hotel & Restaurant

Weber's Hotel & Restaurant

4 out of 5
Lakewood
Save 100% on your flight
Price was $1,419, price is now $939 per person
$939
per person
Sep 24 - Sep 27
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Detroit (DTW)
The Townsend Hotel

The Townsend Hotel

4 out of 5
Save 100% on your flight
Price was $997, price is now $699 per person
$699
per person
Nov 5 - Nov 8
found 22 hours ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)

Pittsfield Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express and Suites Detroit/Sterling Heights by IHG

Holiday Inn Express and Suites Detroit/Sterling Heights by IHG

2.5 out of 5
Price was $560, price is now $389 per person
$389
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
Trumbull and Porter Hotel

Trumbull and Porter Hotel

3.5 out of 5
Corktown
Save 100% on your flight
Price was $965, price is now $548 per person
$548
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
Hotel Houze Detroit Downtown

Hotel Houze Detroit Downtown

3 out of 5
Downtown Detroit
Save 100% on your flight
Price was $796, price is now $554 per person
$554
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)
Hotel Indigo Detroit Downtown by IHG

Hotel Indigo Detroit Downtown by IHG

3.5 out of 5
Downtown Detroit
Save 100% on your flight
Price was $807, price is now $564 per person
$564
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Detroit (DTW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Aug 31 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
DTW
Detroit Metropolitan Wayne County
$68 Roundtrip, found 4 days ago
$68
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Aug 31 from Hartsfield-Jackson Atlanta Intl. to Detroit Metropolitan Wayne County, returning Tue, Sep 1, priced at $68 found 4 days ago
Frontier Airlines
Tue, Oct 27 - Wed, Nov 18
DFW
Dallas-Fort Worth Intl.
DTW
Detroit Metropolitan Wayne County
$76 Roundtrip, found 1 hour ago
$76
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to Detroit Metropolitan Wayne County, returning Wed, Nov 18, priced at $76 found 1 hour ago
Frontier Airlines
Tue, Sep 22 - Wed, Sep 23
MCO
Orlando Intl.
DTW
Detroit Metropolitan Wayne County
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Orlando Intl. to Detroit Metropolitan Wayne County, returning Wed, Sep 23, priced at $100 found 2 days ago
Frontier Airlines
Tue, Sep 29 - Sun, Oct 11
FLL
Fort Lauderdale - Hollywood Intl.
DTW
Detroit Metropolitan Wayne County
$105 Roundtrip, found 1 day ago
$105
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Fort Lauderdale - Hollywood Intl. to Detroit Metropolitan Wayne County, returning Sun, Oct 11, priced at $105 found 1 day ago