Old Mansions - Vacation Rentals in Chestnut Hill

Modern townhome,Boston vacation,2 bath,pkg,deck From US $367
         

9.8 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
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
Rare Find in Boston's Hippest Neighborhood From US $866
         

10.0 (102 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Remodeled Spacious Apartment in Perfect Location From US $720
         

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

10.0 (25 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Budget-Friendly Basement 2BR Retreat From US $188
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Chestnut Hill

Over 670+ Luxury Places to Stay in or Near Chestnut Hill
Well-Lit Bedroom near Transit and Charles River From US $1,890
         

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New
Apartment
  • Air Conditioner
  • Security/Safety
  • Child Friendly
Sleek Boston Home | Near T From US $1,456
         

Minutes to Boston College From US $1,308
         

Gorgeous 5 bed Historic Boston Home From US $1,250
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Top-Rated Vacation Rentals with a Pool in Chestnut Hill

Over 66+ Top-Rated Vacation Rentals with a Pool in or Near Chestnut Hill
Bright Brighton 1BR w/W/D, Doorman, near T + Shopping, by Blueground From US $179
         

The Pistachio Room at TPH - Boston From US $121
         

9.6 (60 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 $104
         

9.6 (25 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
"The In & Out Room" at TPH - Boston From US $162
         

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

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 225+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
Steps to Longwood Medical,MBTA,Boston,shopping,pkg From US $222
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Forest Hill condos -Boston From US $503
         

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9.4 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
182 Heath st From US $163
         

3.6 (4 Reviews)
Apartment
  • Pet Friendly
  • Child Friendly
  • Internet
Newly furnished 1 bed, 1 bath. Views of the whole city! From US $153
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Bed 3 bath Boston Condo From US $338
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Nice 2bd/1.5ba Next to BU 1934 From US $538
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Modern Condo Walk-Out Basement Near Train From US $314
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1BR Private Unit w/Patio & Parking From US $264
         

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

Large Vacation Homes & Villas in Chestnut Hill

Over 64+ Large Vacation Homes & Villas in or Near Chestnut Hill
Mid-Century Glam Retreat, Near T From US $356
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
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 $491
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Historic house renovated for modern convenience From US $450
         

9.8 (134 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Glamorous Luxury Apartment, Near T From US $353
         

9.8 (26 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Glamorous Treetop Escape | near T From US $464
         

9.8 (11 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 209+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Nice 2bd/1.5ba near BU 6648 From US $289
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
A Stylish Stay w/a Queen Bed, Heated Floors. #21 From US $299
         

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

9.4 (1034 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Gorgeous 2BR Next to BU 7488 From US $274
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
2bd/1.5ba Next to BU 1183 From US $267
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 9837 From US $252
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
The Arcadian powered by Sonder | Double Bunk Room w/Corridor View From US $196
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Gorgeous 2bd/1.5ba Next to BU 8707 From US $258
         

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Chestnut Hill Varoom and Airbnb Places to Stay Under $200

Over 260+ Chestnut Hill Varoom 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 $153
         

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8.2 (625 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming room in a 2-bedroom townhome with AC, WiFi in fantastic central Boston From US $177
         

Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village From US $185
         

Renovated 2B, In-unit Laundry, Longwood, 1st Flr From US $185
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sun-filled 1 bed, 1 bath in Brookline Village From US $168
         

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

Instantly Bookable Vacation Homes in Chestnut Hill

Over 341+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
The Arbor Retreat From US $371
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sweet House with yard at prime location From US $397
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Stylish & Cozy Boston Retreat Near Train Station, Parks & Cafés From US $374
         

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

About Chestnut Hill Vacation Rentals

With more than 679 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Old Mansions 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 Old Mansions 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 560.52 ft² on average, with prices averaging $332 a night.

Old Mansions 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 403
Vacation Homes 175
Hotels with Suites 51
B&B 6
Hostels 4
Others 1
Villas 1

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

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