Old Mansions - Vacation Rentals in Chestnut Hill

Property Image From $89
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $38
         

10.0 (20 Reviews)
Resort
  • Air Conditioner
  • Guest Services
Property Image From $151
         

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10.0 (65 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Property Image From $822
         

10.0 (99 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $636
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Property Image From $566
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

Luxury Places to Stay in Chestnut Hill

Over 779+ Luxury Places to Stay in or Near Chestnut Hill
Property Image From $3,746
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $1,890
         

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New
Apartment
  • Air Conditioner
  • Security/Safety
  • Child Friendly
Property Image From $1,392
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Property Image From $1,308
         

Property Image
New
From $1,249
         

Top-Rated Vacation Rentals with a Pool in Chestnut Hill

Over 53+ Top-Rated Vacation Rentals with a Pool in or Near Chestnut Hill
Property Image From $178
         

10.0 (24 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $184
         

10.0 (21 Reviews)
Hostel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $771
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $743
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $505
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $234
         

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 231+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
Property Image From $153
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $503
         

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9.4 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $505
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $163
         

3.6 (4 Reviews)
Apartment
  • Pet Friendly
  • Child Friendly
  • Internet
Property Image From $285
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Property Image From $211
         

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9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Property Image From $272
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $674
         

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8.9 (169 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chestnut Hill

Over 59+ Large Vacation Homes & Villas in or Near Chestnut Hill
Property Image From $308
         

9.3 (91 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Property Image From $391
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Property Image From $508
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Property Image From $111
         

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8.8 (201 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From $453
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Property Image From $455
         

9.8 (129 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 204+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Property Image From $257
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $299
         

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8.5 (43 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Property Image From $316
         

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9.4 (426 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Property Image From $237
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $299
         

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7.6 (8 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Property Image From $220
         

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9.2 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $236
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $290
         

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9.0 (208 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Chestnut Hill Varoom and Airbnb Places to Stay Under $200

Over 315+ Chestnut Hill Varoom and Airbnb Places to Stay Under $200
Property Image From $172
         

Property Image From $157
         

Property Image From $37
         

10.0 (20 Reviews)
Resort
  • Air Conditioner
  • Guest Services
Property Image From $156
         

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7.4 (746 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $73
         

9.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Property Image From $184
         

9.6 (54 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Property Image From $167
         

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8.7 (15 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Guest Services

Instantly Bookable Vacation Homes in Chestnut Hill

Over 339+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Property Image From $396
         

10.0 (17 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From $451
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $326
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From $486
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $478
         

10.0 (1 Review)
Apartment
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
Property Image From $322
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $258
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

About Chestnut Hill Vacation Rentals

With more than 788 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 509.9 ft² on average, with prices averaging $317 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 456
Vacation Homes 173
Hotels with Suites 55
Resorts 53
B&B 7
Hostels 4
Others 2
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