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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington

2.5 out of 5
Save 100% on your flight
Price was $851, price is now $586 per person
$586
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Woburn. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Burlington Mall and MarketStreet Lynnfield are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Price was $2,966, price is now $1,461 per person
$1,461
per person
Aug 21 - Aug 26
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 Boston Harbor are located nearby.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $2,045, price is now $1,173 per person
$1,173
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,647, price is now $1,700 per person
$1,700
per person
Jul 26 - Jul 30
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nobadeer Beach and Madequecham Pond are located nearby.
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $3,727, price is now $2,478 per person
$2,478
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Red River Beach and Forest Beach are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,373, price is now $920 per person
$920
per person
Aug 21 - Aug 26
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 Boston Common are located nearby.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,096, price is now $738 per person
$738
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
The Charles Hotel

The Charles Hotel

4 out of 5
Save 100% on your flight
Price was $1,820, price is now $1,231 per person
$1,231
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was $974, price is now $683 per person
$683
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip non-stop 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 $1,788, price is now $980 per person
$980
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,647, price is now $1,700 per person
$1,700
per person
Jul 26 - Jul 30
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,303, price is now $851 per person
$851
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $2,045, price is now $1,173 per person
$1,173
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,966, price is now $1,461 per person
$1,461
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was $2,077, price is now $1,193 per person
$1,193
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $5,751, price is now $3,534 per person
$3,534
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)

Top Flight Deals

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

Breeze Airways
Sun, Aug 30 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$169 Roundtrip, found 6 days ago
$169
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $169 found 6 days ago
Breeze Airways
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$192 Roundtrip, found 1 hour ago
$192
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Portsmouth Intl., returning Sun, Dec 13, priced at $192 found 1 hour ago
American Airlines
Tue, Aug 4 - Wed, Aug 12
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$225 Roundtrip, just found
$225
Roundtrip
just found
Select American Airlines flight, departing Tue, Aug 4 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Wed, Aug 12, priced at $225 just found
JetBlue Airways
Wed, Jun 17 - Mon, Jun 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$248 Roundtrip, found 14 hours ago
$248
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Wed, Jun 17 from Orlando Intl. to Manchester-Boston Regional, returning Mon, Jun 29, priced at $248 found 14 hours ago