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Chesterfield Vacation Packages

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Chesterfield Flight + Hotel Packages

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
Save 100% on your flight
Price was $1,031, price is now $727 per person
$727
per person
Jun 24 - Jun 27
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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Save 100% on your flight
Price was $1,298, price is now $745 per person
$745
per person
Jul 25 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,816, price is now $1,132 per person
$1,132
per person
Aug 6 - Aug 9
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 New England Aquarium and Boston Harbor are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $1,750, price is now $1,146 per person
$1,146
per person
Jul 25 - Jul 30
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.
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,318, price is now $879 per person
$879
per person
Aug 6 - Aug 9
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 clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,516, price is now $1,742 per person
$1,742
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
The Groton Inn

The Groton Inn

3.5 out of 5
Save 100% on your flight
Price was $1,364, price is now $954 per person
$954
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this business-friendly hotel in Groton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Legion Field and Nashoba Paddler are located nearby.
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $4,066, price is now $2,862 per person
$2,862
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this beach guesthouse in East Wareham. Enjoy free WiFi, a private beach, and free bicycles on site. Popular attractions Onset Bay Center - Buzzards Bay Coalition and Onset Beach are located nearby.

Chesterfield 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
Save 100% on your flight
Price was $1,005, price is now $647 per person
$647
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,154, price is now $1,324 per person
$1,324
per person
Jun 24 - Jun 27
found 1 day 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 $1,816, price is now $1,132 per person
$1,132
per person
Aug 6 - Aug 9
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 $2,516, price is now $1,742 per person
$1,742
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)

Chesterfield Vacation Packages 5-7 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
Save 100% on your flight
Price was $1,298, price is now $745 per person
$745
per person
Jul 25 - Jul 30
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
Price was $4,313, price is now $2,302 per person
$2,302
per person
Jul 20 - Jul 27
found 16 hours ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,566, price is now $1,532 per person
$1,532
per person
Jul 1 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $2,655, price is now $1,684 per person
$1,684
per person
Jul 1 - Jul 6
found 9 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)

Top Flight Deals

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

American Airlines
Tue, Aug 11 - Tue, Aug 25
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 3 hours ago
$237
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Aug 11 from Los Angeles Intl. to Logan Intl., returning Tue, Aug 25, priced at $237 found 3 hours ago
American Airlines
Sat, May 30 - Tue, Jun 2
PDX
Portland Intl.
BOS
Logan Intl.
$242 Roundtrip, just found
$242
Roundtrip
just found
Select American Airlines flight, departing Sat, May 30 from Portland Intl. to Logan Intl., returning Tue, Jun 2, priced at $242 just found
Bargain Flight
Sat, May 23 - Mon, Jun 1
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$313 Roundtrip, found 3 days ago
$313
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sat, May 23 from Los Angeles Intl. to Bradley Intl., returning Mon, Jun 1, priced at $313 found 3 days ago
Delta
Tue, Jun 9 - Tue, Jun 16
PDX
Portland Intl.
BDL
Bradley Intl.
$404 Roundtrip, found 3 days ago
$404
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jun 9 from Portland Intl. to Bradley Intl., returning Tue, Jun 16, priced at $404 found 3 days ago