Chestnut Hill Vacation Packages 2025/2026 from $379

Chestnut Hill flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

Save 100% on your flight

$379

per person

Nov 8 - Nov 10

found 5 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

D. Hotel Suites & Spa

$379

per person

Dec 19 - Dec 22

found 5 hours ago

Roundtrip flight included

Tampa (TPA) to Boston (BOS)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. You'll appreciate the gym, bar/lounge, and laundry facilities.

Beacon Hill Hotel

Beacon Hill

Save 100% on your flight

$811

per person

Nov 26 - Dec 1

found 1 day ago

Roundtrip flight included

Houston (IAH) to Boston (BOS)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free continental breakfast is served.

Pennyweight Hotel Boston, Curio Collection by Hilton

West End

Save 100% on your flight

$726

per person

Dec 4 - Dec 9

found 20 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This hotel features a 24-hour gym and a bar/lounge. WiFi in public areas is free. Valet parking, express check-out, and dry cleaning are also offered.

Cambria Hotel & Suites Plymouth

Save 100% on your flight

$390

per person

Nov 8 - Nov 12

found 6 hours ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

A 24-hour gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A convenience store is provided and the front desk is staffed around-the-clock.

Top Chestnut Hill hotels deals

Seaport Hotel Boston

1 Seaport Lane, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$280 nightly

$325 total

Sep 28 - Sep 29

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the steam room, bar/lounge, and concierge services.

Pool

Pet friendly

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$294 nightly

$342 total

Sep 28 - Sep 29

Total with taxes and fees

A full-service spa, 4 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. You'll appreciate the 24-hour gym, poolside bar, and snack bar/deli.

Pool

Hot Tub

citizenM Boston North Station

70 Causeway Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$234 nightly

$273 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

The Dagny Boston

89 Broad Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$302 nightly

$351 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a library, and a computer station are also on offer.

Pet friendly

Free WiFi

The Revolution Hotel

40 Berkeley Street, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$220 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Pet friendly

Free WiFi

Hilton Boston Logan Airport

One Hotel Drive, Boston, MA

Free Cancellation

Reserve now, pay when you stay

$303 nightly

$353 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Pool

Free airport shuttle

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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.

Popular places to visit

One of the prettiest & highly competitive colleges in the Boston area.

Boston College

Take a campus tour or just explore the area around Boston College, a top college in Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Alumni Stadium

Catch an event at Alumni Stadium during your trip to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.

Conte Forum

Catch an event at Conte Forum during your trip to Boston. Experience the area's art scene and live music.

Frequently asked questions

How much are vacation packages to Chestnut Hill?

Starting at just $379, hotel and flight packages are the perfect way to make your vacation budget stretch further. Watch out Chestnut Hill — here you come!

Where can I get the best vacation package deals for Chestnut Hill?

Look no further than Travelocity. With access to 400 airlines and a massive 1,000,000 properties across the globe, selecting the perfect Chestnut Hill package deal couldn't be easier.

Why should I book my Chestnut Hill vacation package via Travelocity?

With our Price Match Guarantee, we'll match any cheaper price you're able to find. Add on our 24/7 customer support and superb service and the vacation you've been dreaming of is well within reach.

Will I save money on my Chestnut Hill car rental if I book it with hotels and flights?

Combining your flight, hotel and car into a Chestnut Hill vacation package is a great way to score better prices. Plus, having your own set of wheels gives you total freedom to get to all those landmarks you're itching to see. Located 35 mi from Chestnut Hill, Plymouth Rock is one attraction that should be on your itinerary. Buckle up and make a day trip of it.

Which airport is best for Chestnut Hill?

Logan Intl. Airport (BOS) is popular. You'll find it approximately 8 mi northeast of Chestnut Hill. Other options worth considering are T.F. Green Airport (PVD) (45 mi away from central Chestnut Hill) and Manchester-Boston Regional Airport (MHT) (45 mi away from central Chestnut Hill).

Where should I stay when visiting Chestnut Hill?

The Trendy Chestnut Hill 1BR w/ W/D & Gym, nr Hancock Village, by Blueground is the number one choice of many visitors. Book as soon as possible before it's too late.