Chestnut Hill Vacations from $503
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Your Chestnut Hill Vacation
With plenty of highlights as well as hidden gems, this city is best experienced with a Chestnut Hill vacation package. Find somewhere to stay in Downtown Boston, which is great for nightlife, shopping and bars and pubs. Fill your schedule with visits to Boston College, Paradise Rock Club and Agganis Arena, some of the attractions you simply have to see during your trip to Chestnut Hill. Browse Expedia's wide range of travel options and start organizing your perfect vacation to Chestnut Hill today.
The Latest Chestnut Hill Vacation Packages
- Sea Crest Beach Resort
Jan 15 - Jan 18Sea Crest Beach Resort + Flight
North Falmouth3 nights3.5 star property7.6/10 - Good (550 reviews)Roundtrip • Miami (MIA) - Boston (BOS)MIA - BOS • Nonstop BOS - MIA • Nonstop$710$503found 1 day agoper traveler - Boston Lodge and Suites
Dec 21 - Dec 26Boston Lodge and Suites + Flight
Dorchester5 nights4.0 star property8.4/10 - Very good (194 reviews)"The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The..."Reviewed October 17, 2026Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • Nonstop$1,565$769found 18 hours agoper traveler - Boston Harbor Hotel
Jan 25 - Jan 29Boston Harbor Hotel + Flight
North End4 nights5.0 star property9.8/10 - Exceptional (1,002 reviews)Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • 1 stop$1,994$1,147found 1 day agoper traveler - Iris Hotel Cape Cod
Jan 15 - Jan 18Iris Hotel Cape Cod + Flight
Falmouth3 nights3.0 star property8.4/10 - Very good (438 reviews)Roundtrip • Los Angeles (LAX) - Boston (BOS)LAX - BOS • Nonstop BOS - LAX • Nonstop$839$517found 2 hours agoper traveler - The Newbury Boston
Dec 21 - Dec 26The Newbury Boston + Flight
Back Bay5 nights5.0 star property9.4/10 - Exceptional (746 reviews)Roundtrip • Dallas (DFW) - Boston (BOS)DFW - BOS • Nonstop BOS - DFW • Nonstop$2,423$1,630found 2 hours agoper traveler
Where to stay in Chestnut Hill
Downtown Boston
Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.
Back Bay
Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.
Seaport District
Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.
Beacon Hill
Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.
North End
Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.
What to do near Chestnut Hill
Boston CityPASS®: Admission to Top 4 Attractions
Boston Haunted Tour : Ghosts & Gravestones
City Cruises Boston: Historic Sightseeing Cruise
Chestnut Hill Hotel Deals
Hampton Inn & Suites Watertown Boston
Hampton Inn & Suites Watertown Boston"Poor housekeeping standards. I arrived on Monday 10/26 and checked in to 3 successive rooms where all the beds had been made up with dirty sheets with hairs, debris, food crumbs, and a small leaf/ twig all plainly visible. The bed was clean in the 4th room although there were hairs on the toilet seat which I cleaned myself. I would have canceled the reservation and moved elsewhere but I arrived after midnight and had a full schedule over the next several days so I was stuck there. I reported...
"Perfect! I'd definitely come back! Everything is clean and they have everything you need! Coffee and tea at the front desk—perfect!"
Sheraton Boston Needham Hotel
Sheraton Boston Needham Hotel
"Place was clean and surprisingly quiet for how many people were staying there at the time. Location was perfect for an easy commute via the T when it was up and running (it was down for service). The continental breakfast available was light and lacked variety, but there are plenty of walkable restaurants in the area. Our room did not have a closet and we were not able to hang up our clothing due to the fact that the set of hooks provided, in place of our closet, were clearly not attached to...
"Beautiful"
"👍"
"Charming hotel with very nice accommodations. Located in a great area of Boston, walking distance to many places and a short drive to so much."
DoubleTree Suites by Hilton Hotel Boston - Cambridge
DoubleTree Suites by Hilton Hotel Boston - CambridgeFind out more about Chestnut Hill
Things to do near Chestnut Hill
Chestnut Hill offers a delightful mix of city and cultural experiences perfect for family vacations. Visitors can enjoy outdoor adventures, friendly hikes, and explore local parks. The area also features a popular shopping mall and various shopping centers, making it easy to indulge in retail therapy. With its educational attractions and vibrant community, Chestnut Hill is a fantastic destination for those seeking a blend of leisure and exploration.
Shopping
In Chestnut Hill, you can enjoy shopping at Harvard Square and Copley Place, both offering a mix of entertainment and family-friendly vibes. Don’t miss John Lewis, Inc, for unique gifts and souvenirs. Each destination is a short drive away, making them convenient for your shopping needs.
Recreation
Experience the vibrant atmosphere at House of Blues Boston, just 4 miles from Chestnut Hill, where live music fills the air. For sports enthusiasts, Agganis Arena, located 3 miles away, offers thrilling events. Enjoy a cultural outing at Coolidge Corner Theatre, also 3 miles from Chestnut Hill, showcasing films and entertainment.
Adventure
Experience the fun at LEGOLAND® Discovery Center, an arcadeAdventureZone 7 miles from Chestnut Hill, perfect for family adventures. Explore the scenic Irish Heritage Trail, a hikingTrail 6 miles away, offering outdoor beauty. Needham Bowlaway, an arcadeAdventureZone 5 miles from Chestnut Hill, promises excitement for the whole family.
Nightlife
For a vibrant nightlife in Chestnut Hill, check out Cambridge Common, a lively pub 5 miles away, perfect for entertainment and romance. Alternatively, visit Park-9 Dog Bar, 8 miles away, where you can enjoy drinks in a fun atmosphere with a unique twist. Both promise a memorable evening.
Find the best attractions near Chestnut Hill
Chestnut Hill, Newton, Massachusetts, offers a delightful blend of city and cultural experiences perfect for family vacations. Visitors can explore historic colleges, modern universities, and urban parks, including the scenic Chestnut Hill Reservoir. With panoramic views and major attractions, this charming area caters to travelers seeking enriching experiences and memorable outings. Whether you're strolling through local parks or soaking in the vibrant atmosphere, Chestnut Hill promises an enjoyable getaway for all.
- Fenway Park: Experience the thrill of America's pastime at Fenway Park, the oldest ballpark in Major League Baseball. Located 4 miles from Chestnut Hill, it offers a unique blend of sports and culture, where you can catch a Red Sox game or take a guided tour to explore its rich history and iconic features, like the Green Monster.
- Harvard University: Just 4 miles away, Harvard University invites you to stroll through its historic campus, filled with stunning architecture and lush greenery. Immerse yourself in the rich culture and intellectual vibes as you explore museums, libraries, and galleries, making it a perfect spot for history buffs and art lovers.
- Boston Common: At 6 miles from Chestnut Hill, Boston Common is America’s oldest public park, offering a beautiful outdoor escape in the heart of the city. Enjoy family-friendly activities, scenic walking paths, and vibrant gardens, making it an ideal spot to relax, picnic, or take in seasonal events.
Best time to go to Chestnut Hill
The best time to visit Chestnut Hill can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chestnut Hill falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Chestnut Hill falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.
Tips to save on your trip to Chestnut Hill
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chestnut Hill.
- Consider traveling to Chestnut Hill during the low season (December to February) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.