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Chatham Vacation Packages

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Chatham Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
XStay Suites Mansfield

XStay Suites Mansfield

2 out of 5
Price was $524, price is now $377 per person
$377
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
Stay at this hotel in Mansfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Xfinity Center and National Black Doll Museum are located nearby.
I had a proble

Reviewed on Oct 14, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Price was $1,445, price is now $732 per person
$732
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Ashworth by the Sea

Ashworth by the Sea

3 out of 5
Save 100% on your flight
Price was $1,155, price is now $712 per person
$712
per person
Nov 27 - Dec 5
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this beach hotel in Hampton. Enjoy 3 restaurants, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hampton Beach and Hampton Beach Casino are located nearby.
The hotel is right across from the beach. Lovely place

Reviewed on Oct 14, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,082, price is now $673 per person
$673
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip 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 Faneuil Hall Marketplace and Boston Harbor are located nearby.
Great location

Reviewed on Oct 13, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $2,910, price is now $1,895 per person
$1,895
per person
Dec 26 - Jan 1
found 18 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
Excellent hotel to stay in for experiencing Boston. Great location, excellent service, wonderful staff.

Reviewed on Oct 14, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Price was $1,107, price is now $773 per person
$773
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Harbor and Faneuil Hall Marketplace are located nearby.

New Bedford Harbor Hotel

New Bedford Harbor Hotel

3 out of 5
Save 100% on your flight
Price was $571, price is now $399 per person
$399
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)
Stay at this hotel in New Bedford. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Judith Klein Art Gallery and Zeiterion Theatre are located nearby.

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,519 per person
$1,519
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in. On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.

Reviewed on Oct 6, 2026

Chatham Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was $946, price is now $637 per person
$637
per person
Dec 18 - Dec 21
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,445, price is now $732 per person
$732
per person
Nov 28 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,953, price is now $1,006 per person
$1,006
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,388, price is now $882 per person
$882
per person
Jan 10 - Jan 13
found 3 hours ago
Roundtrip flight included
Raleigh (RDU) to Boston (BOS)

Chatham Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was $1,720, price is now $986 per person
$986
per person
Dec 23 - Dec 30
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,811, price is now $1,625 per person
$1,625
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,910, price is now $1,895 per person
$1,895
per person
Dec 26 - Jan 1
found 18 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,830, price is now $1,904 per person
$1,904
per person
Dec 26 - Jan 1
found 18 hours ago
Roundtrip flight included
St. Louis (STL) to Boston (BOS)

Top Flight Deals

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

Frontier Airlines
Wed, Nov 4 - Sat, Nov 14
LAX
Los Angeles Intl.
BOS
Logan Intl.
$278 Roundtrip, found 9 hours ago
$278
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Nov 4 from Los Angeles Intl. to Logan Intl., returning Sat, Nov 14, priced at $278 found 9 hours ago
Bargain Flight
Fri, Jan 15 - Sat, Jan 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$300 Roundtrip, found 3 days ago
$300
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Jan 15 from Los Angeles Intl. to Logan Intl., returning Sat, Jan 23, priced at $300 found 3 days ago
Delta
Tue, Nov 24 - Thu, Nov 26
LAX
Los Angeles Intl.
BOS
Logan Intl.
$333 Roundtrip, found 1 day ago
$333
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 24 from Los Angeles Intl. to Logan Intl., returning Thu, Nov 26, priced at $333 found 1 day ago
Bargain Flight
Fri, Nov 6 - Wed, Nov 11
PDX
Portland Intl.
BOS
Logan Intl.
$341 Roundtrip, found 6 hours ago
$341
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Fri, Nov 6 from Portland Intl. to Logan Intl., returning Wed, Nov 11, priced at $341 found 6 hours ago