Castle In Hawaii - Vacation Rentals in Chestnut Hill

Roslindale village condos From US $674
         

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8.9 (176 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Gorgeous 5 bedroom Boston Home From US $1,325
         

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New
Villa
  • Air Conditioner
  • Parking
  • Barbecue/Outdoor Cooking

Luxury Places to Stay in Chestnut Hill

Over 727+ Luxury Places to Stay in or Near Chestnut Hill
New Luxury Renovation | Near T From US $2,276
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Luxury 5BR APT | Boston From US $2,178
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV
Sleek Boston Home | Near T From US $1,550
         

Top-Rated Vacation Rentals with a Pool in Chestnut Hill

Over 66+ Top-Rated Vacation Rentals with a Pool in or Near Chestnut Hill
The Sanctuary at TPH - Boston From US $178
         

10.0 (27 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Brand New Modern Private House in Newton. From US $996
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The Pistachio Room at TPH - Boston From US $172
         

9.6 (63 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
The Sunset Room at TPH - Boston From US $178
         

9.6 (25 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
The Tower Room at TPH - Boston From US $178
         

9.6 (25 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
"The In & Out Room" at TPH - Boston From US $169
         

9.4 (13 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 241+ Pet-Friendly Vacation Rentals in or Near 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
182 Heath st From US $163
         

3.6 (4 Reviews)
Apartment
  • Pet Friendly
  • Child Friendly
  • Internet
Budget-Friendly Basement 2BR Retreat From US $340
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
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 $590
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Nice 2bd/1.5ba Next to BU 4119 From US $512
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba Next to BU 1183 From US $530
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Cozy 1BR Private Unit w/Patio & Parking From US $469
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Chestnut Hill

Over 70+ Large Vacation Homes & Villas in or Near Chestnut Hill
Boston Single Family House - 19' Train to Back Bay From US $636
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • View
City's Hippest Neighborhood. n From US $965
         

10.0 (102 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Mid-Century Glam Retreat, Near T From US $914
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Modern Boston Condo | near T From US $1,160
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Brookline Haven - Rooftop + Deck + Game Room +T From US $1,460
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Historic house renovated for modern convenience From US $489
         

9.8 (136 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 216+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
A Stylish Stay w/a Queen Bed, Heated Floors. #21 From US $481
         

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8.5 (43 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Hampton Inn & Suites Watertown Boston From US $124
         

9.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Gorgeous 2BR Next to BU 7731 From US $601
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
2bd/1.5ba Next to BU 9013 From US $549
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Nice 2bd/1.5ba near BU 3848 From US $529
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2bd/1.5ba Next to BU 3880 From US $343
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 6369 From US $343
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Beautiful 2bd/1.5ba near BU 8547 From US $417
         

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

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

Over 213+ 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 (65 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Huge 2 bed, 2 bath new apartment with private terrace! From US $195
         

9.6 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
The King's Room at TPH - Boston From US $178
         

9.2 (24 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Chestnut Hill

Over 356+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Remodeled Spacious Apartment in Perfect Location From US $757
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Charming Tree Top Victorian - Two Bedroom Retreat From US $486
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Luxury 3brm/1bath Duplex in JP From US $629
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Arbor Retreat From US $955
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Old Brookline Charm 5 min Longwood In-Unit Laundry From US $349
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village From US $237
         

About Chestnut Hill Vacation Rentals

With more than 2 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Castleinhawaii 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 Castleinhawaii 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 2614.28 ft² on average, with prices averaging $1,000 a night.

Castleinhawaii 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 1
Villas 1

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

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

There are a lot of options in Chestnut Hill. If you plan on staying in the Chestnut Hill area, consider making a reservation for a few nights at one of these properties as these have been rated 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 2 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.