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Chestnut Hill Vacation Packages

Chestnut Hill 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.
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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was $1,299, price is now $842 per person
$842
per person
Jul 14 - Jul 18
found 1 day ago
Roundtrip 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.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Price was $1,194, price is now $846 per person
$846
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $1,876, price is now $1,330 per person
$1,330
per person
Jun 29 - Jul 3
found 4 hours ago
Roundtrip non-stop 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.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was $1,274, price is now $905 per person
$905
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
Price was $1,564, price is now $1,114 per person
$1,114
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $3,078, price is now $2,227 per person
$2,227
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.

3-4 Night Vacations in Chestnut Hill

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 $945, price is now $651 per person
$651
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip non-stop 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 $1,753, price is now $1,196 per person
$1,196
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $1,876, price is now $1,330 per person
$1,330
per person
Jun 29 - Jul 3
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Summer House Hotel

Summer House Hotel

2 out of 5
Save 100% on your flight
Price was $2,281, price is now $1,652 per person
$1,652
per person
Jun 29 - Jul 3
found 4 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)

5-7 Night Vacations in Chestnut Hill

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)
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)
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was $1,891, price is now $1,208 per person
$1,208
per person
Jul 10 - Jul 16
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Price was $1,194, price is now $846 per person
$846
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Cheap Hotel Deals in Chestnut Hill

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
Opens in a new windowSeaport Hotel Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
Opens in a new windowThe Revolution Hotel
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Opens in a new windowOmni Boston Hotel at the Seaport
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The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
Opens in a new windowThe Godfrey Hotel Boston
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...
Opens in a new windowThe Dagny Boston
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
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 ...
Opens in a new windowThe Langham, Boston
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
161 Devonshire St Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Opens in a new windowClub Quarters Hotel Faneuil Hall, Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
Opens in a new windowThe Midtown Hotel MOD Collection by Sonesta
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

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

JetBlue Airways
Tue, Aug 11 - Thu, Sep 3
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 15 hours ago
$237
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Los Angeles Intl. to Logan Intl., returning Thu, Sep 3, priced at $237 found 15 hours ago
Bargain Flight
Sat, Jun 6 - Sat, Jun 13
PDX
Portland Intl.
BOS
Logan Intl.
$302 Roundtrip, found 5 hours ago
$302
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Sat, Jun 6 from Portland Intl. to Logan Intl., returning Sat, Jun 13, priced at $302 found 5 hours ago
Delta
Tue, Jun 23 - Fri, Jul 24
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,045 Roundtrip, found 4 hours ago
$1,045
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jun 23 from Hong Kong Intl. to Logan Intl., returning Fri, Jul 24, priced at $1,045 found 4 hours ago
Hainan Airlines
Tue, Sep 15 - Wed, Sep 23
PVG
Pudong Intl.
BOS
Logan Intl.
$1,098 Roundtrip, found 17 hours ago
$1,098
Roundtrip
found 17 hours ago
Select Hainan Airlines flight, departing Tue, Sep 15 from Pudong Intl. to Logan Intl., returning Wed, Sep 23, priced at $1,098 found 17 hours ago