Blue Flag Usvi - Vacation Rentals in Chestnut Hill

Renovated, Chic, one bed, Sleeps 4,Steps to Transit From US $89
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
A Village Bed and Breakfast From US $151
         

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10.0 (70 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
City's Hippest Neighborhood. From US $847
         

10.0 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Remodeled Spacious Apartment in Perfect Location From US $751
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
The Sanctuary at TPH - Boston From US $178
         

10.0 (30 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Budget-Friendly Basement 2BR Retreat From US $310
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Charming Tree Top Victorian - Two Bedroom Retreat From US $481
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chestnut Hill

Over 742+ Luxury Places to Stay in or Near Chestnut Hill
Sleek Boston Home | Near T From US $1,767
         

New Luxury Renovation | Near T From US $1,600
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Brookline Haven - Rooftop + Deck + Game Room +T From US $1,450
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Chestnut Hill

Over 65+ Top-Rated Vacation Rentals with a Pool in or Near Chestnut Hill
Brand New Modern Private House in Newton. From US $1,001
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The Tower Room at TPH - Boston From US $178
         

9.8 (26 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
The Pistachio Room at TPH - Boston From US $212
         

9.6 (68 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
The Sunset Room at TPH - Boston From US $184
         

9.6 (26 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Boston Watertown From US $208
         

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9.2 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 244+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
Newly furnished 1 bed, 1 bath. Views of the whole city! From US $153
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious City Retreat, 3BR From US $351
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
182 Heath st From US $163
         

3.6 (4 Reviews)
Apartment
  • Pet Friendly
  • Child Friendly
  • Internet
Modern Condo First Floor Boston From US $465
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Nice 2bd/1.5ba Next to BU 7qn5 From US $481
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy 1BR Private Unit w/Patio & Parking From US $468
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba Next to BU 74c3 From US $464
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Old Brookline Charm 5 min Longwood In-Unit Laundry From US $788
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chestnut Hill

Over 72+ Large Vacation Homes & Villas in or Near Chestnut Hill
Natalie House From US $308
         

9.4 (102 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • View
4BR/4BA | Parking + Chef’s Kitchen | Near BU/BC From US $1,195
         

Modern Boston Condo | near T From US $960
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Historic house renovated for modern convenience From US $494
         

9.8 (139 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
FIFA World Cup Stay! Luxury 6,000 Sq Ft Home Near Boston From US $1,251
         

88 Boylston Street · Skyrise Two Stories - Centrally Located From US $780
         

9.4 (43 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 223+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Nice 2bd/1.5ba near BU uutt From US $535
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
A Stylish Stay w/a Queen Bed, Heated Floors. #21 From US $481
         

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7.8 (46 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Hampton Inn & Suites Watertown Boston From US $176
         

9.4 (1066 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
2bd/1.5ba Next to BU yolt From US $511
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 67ne From US $452
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2bd/1.5ba Next to BU ag71 From US $422
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU up8y From US $502
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba near BU 6zok From US $431
         

7.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Chestnut Hill Vacation Rentals and Airbnb Places to Stay Under $200

Over 212+ Chestnut Hill Vacation Rentals and Airbnb Places to Stay Under $200
2 bedroom condo close to Boston and Cambridge with free parkings From US $157
         

Coolidge Corner Guest House From US $179
         

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8.2 (637 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
"The In & Out Room" at TPH - Boston From US $178
         

9.0 (14 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Chestnut Hill

Over 365+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Luxury 3brm/1bath Duplex in JP From US $900
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Arbor Retreat From US $1,164
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Bright & Spacious Boston Retreat From US $479
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village From US $316
         

Sunny 4 Bed/2 Bath Victorian Oasis in the City! From US $660
         

9.8 (155 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV

About Chestnut Hill Vacation Rentals

With more than 751 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Blueflagusvi and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chestnut Hill.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Blueflagusvi Chestnut Hill, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chestnut Hill. Places to stay near Chestnut Hill are 572.37 ft² on average, with prices averaging US $384 a night.

Blueflagusvi makes it easy and safe to find and compare vacation rentals in Chestnut Hill with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chestnut Hill

Type Count
Holiday Apartments 460
Vacation Homes 191
Hotels 50
B&B 6
Hostels 4

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

Pro Tip: Blueflagusvi makes it easy to compare the best listings on Blueflagusvi homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Blueflagusvi homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chestnut Hill.

Weather in Chestnut Hill

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

Chestnut Hill Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chestnut Hill?
How many vacation rentals are available in Chestnut Hill?

Currently, the total number of properties listed in 2026 is over 751 in the Chestnut Hill area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chestnut Hill.