644+ Hotel & Resort Deals in Chestnut Hill |
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Chestnut Hill Hotels, Resorts, and Rentals

About Chestnut Hill Vacation Rentals

There are more than 644 places to stay in Chestnut Hill that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Chestnut Hill.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Chestnut Hill, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Chestnut Hill. Places to stay near Chestnut Hill are 552.74 ft² on average, with prices averaging GB £258 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Chestnut Hill with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Chestnut Hill

Type Count
Holiday Apartments 380
Vacation Homes 171
B&B 6

Use these Quick Filters to Find a Vacation Rental in Chestnut Hill

★ Pro Tip: Hotala.uk has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Chestnut Hill.

Weather in Chestnut Hill, MA

View the weather forecast for Chestnut Hill before booking your Chestnut Hill Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Chestnut Hill's Top Attractions

Hotala.uk can help you find hotels, resorts, and rentals near many of Chestnut Hill's top attractions, neighborhoods, and points of interest.


Boston College
Alumni Stadium
McMullen Museum
Osher Clinical Center
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
Gillette Stadium
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Osher Clinical Center 1,022 Properties
Woodland Heath 814 Properties
Alumni Stadium 740 Properties
Boston College 738 Properties
McMullen Museum 704 Properties
South Brookline 501 Properties

Frequently Asked Questions About Chestnut Hill?

What are the top hotels or resorts in Chestnut Hill?

You have a lot of choices in or near Chestnut Hill. If you need a hotel in the Chestnut Hill area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Chestnut Hill:

How many vacation rentals have private pools in Chestnut Hill?

There are 6 accommodation options with private pools in or near Chestnut Hill. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Chestnut Hill is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Chestnut Hill, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Chestnut Hill:

How many hotels, resorts, or rentals are available in Chestnut Hill?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 644 in the Chestnut Hill area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Chestnut Hill.

Nearby Neighborhood (8) 
Neighborhood Property Count
Brighton Hotel & Resort Deals in Boston, Massachusetts 96
Cleveland Circle Hotel & Resort Deals in Boston, Massachusetts 75
Commonwealth Hotel & Resort Deals in Boston, Massachusetts 32
Newton Corner Hotel & Resort Deals in Boston, Massachusetts 497
Brook Farm Hotel & Resort Deals in Boston, Massachusetts 176
Woodland Heath Hotel & Resort Deals in Boston, Massachusetts 814
Thompsonville Hotel & Resort Deals in Boston, Massachusetts 358
South Brookline Hotel & Resort Deals in Boston, Massachusetts 501

People Also Ask

There are 50 hotels in Chestnut Hill and 551 rentals

Recently Booked Hotels, Resorts, or Rentals in Chestnut Hill