Sell Off Cruises - Vacation Rentals in Chestnut Hill

Remodeled Spacious Apartment in Perfect Location From US $751
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
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
Residence Inn by Marriott Boston Watertown From US $345
         

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9.2 (1004 Reviews)
Hotel
  • 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 $565
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Newly furnished 1 bed, 1 bath. Views of the whole city! From US $153
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Condo First Floor Boston From US $465
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

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
Vintage 5BR apt in Boston with Free Parking From US $1,361
         

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9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety

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
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $287
         

Residence Inn by Marriott Boston Watertown From US $398
         

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8.9 (224 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Sheraton Boston Needham Hotel From US $170
         

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8.8 (1696 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Homewood Suites by Hilton Boston Brookline-Longwood Medical From US $375
         

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 241+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
Cozy 1BR Private Unit w/Patio & Parking From US $468
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
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
Old Brookline Charm 5 minLongwood In-Unit Laundry From US $835
         

10.0 (1 Review)
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
Stylish & Cozy Boston Retreat Near Train Station, Parks & Cafés From US $607
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
2 bedroom condo close to Boston and Cambridge with free parking From US $456
         

9.6 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
3 bed 2 bath Boston Condo From US $461
         

9.4 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chestnut Hill

Over 73+ Large Vacation Homes & Villas in or Near Chestnut Hill
4BR/4BA | Parking + Chef’s Kitchen | Near BU/BC From US $1,195
         

Natalie House From US $308
         

9.4 (102 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • View
Luxury 5BR APT | Boston From US $1,117
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV
City's Hippest Neighborhood. From US $847
         

10.0 (104 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Mid-Century Glam Retreat, Near T From US $865
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 220+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Beautiful 2bd/1.5ba near BU 6zok From US $431
         

7.0 (4 Reviews)
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
Beautiful 2BR Next to BU o6yb From US $490
         

5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2BR Next to BU hhqo From US $496
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Blueground | North Brookline, washer, nr Beacon St From US $395
         

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

Over 215+ 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
         

A Village Bed and Breakfast From US $151
         

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10.0 (70 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Boston vacation,Longwood Medical,mins to MBTA,pkg From US $148
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Chestnut Hill

Over 374+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Bright & Spacious Boston Retreat From US $479
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sunny 4 Bed/2 Bath Victorian Oasis in the City! From US $660
         

9.8 (155 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Walk to Transit & Eats! 'Urban Oasis in Newton' From US $475
         

9.4 (14 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace

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, Selloffcruises 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 Selloffcruises 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 576.24 ft² on average, with prices averaging US $387 a night.

Selloffcruises 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 459
Vacation Homes 191
Hotels 50
B&B 6
Hostels 4
Villas 1

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

Pro Tip: Selloffcruises makes it easy to compare the best listings on Selloffcruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selloffcruises 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

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.