Marthas Vineyard Cottages - 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 (65 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
City's Hippest Neighborhood. n From US $965
         

10.0 (102 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Remodeled Spacious Apartment in Perfect Location From US $757
         

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

10.0 (27 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Budget-Friendly Basement 2BR Retreat From US $340
         

10.0 (20 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Charming Tree Top Victorian - Two Bedroom Retreat From US $486
         

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

Luxury Places to Stay in Chestnut Hill

Over 720+ 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
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  • Balcony/Terrace
Luxury 5BR APT | Boston From US $2,178
         

New
Apartment
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Sleek Boston Home | Near T From US $1,550
         

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 $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
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  • 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
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  • Pool
Residence Inn by Marriott Boston Watertown From US $180
         

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9.2 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 240+ 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 (1 Review)
Apartment
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  • 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 $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
Stylish & Cozy Boston Retreat Near Train Station, Parks & Cafés From US $861
         

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

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
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
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  • TV
Historic house renovated for modern convenience From US $489
         

9.8 (136 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
88 Boylston Street · Skyrise Two Stories - Centrally Located From US $1,044
         

9.6 (42 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Boston Renovation | Near T From US $1,174
         

9.4 (13 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 215+ 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
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
Beautiful 2BR Next to BU 3774 From US $343
         

5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

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

Over 211+ 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 $146
         

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8.2 (630 Reviews)
House
  • 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

Instantly Bookable Vacation Homes in Chestnut Hill

Over 349+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
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
         

2 bedroom condo close to Boston and Cambridge with free parking From US $456
         

9.8 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

About Chestnut Hill Vacation Rentals

With more than 729 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Marthasvineyardcottages 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 Marthasvineyardcottages 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 601.56 ft² on average, with prices averaging $405 a night.

Marthasvineyardcottages 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 444
Vacation Homes 182
Hotels with Suites 52
B&B 6
Hostels 4
Villas 1

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

Pro Tip: Marthasvineyardcottages makes it easy to compare the best listings on Marthasvineyardcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Marthasvineyardcottages 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 729 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.