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

9.8 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Brookline Village, Central Air, 2B, Near Longwood From US $219
         

9.6 (63 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Boston vacation,Longwood Medical,mins to MBTA,pkg From US $147
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
15 minutes to Historic Sights and World Cup Transport. From US $850
         

Remodeled Spacious Apartment in Perfect Location From US $720
         

10.0 (30 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Chestnut Hill

Over 672+ 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
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Sleek Boston Home | Near T From US $1,552
         

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 65+ 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 $170
         

The Pistachio Room at TPH - Boston From US $172
         

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 $178
         

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 224+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
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
Budget-Friendly Basement 2BR Retreat From US $188
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Steps to Longwood Medical,MBTA,Boston,shopping,pkg From US $221
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
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 $341
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Nice 2bd/1.5ba Next to BU 8149 From US $505
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Renovated 1BED, Steps to MBTA, Shops & Restaurants From US $159
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chestnut Hill

Over 64+ 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
Mid-Century Glam Retreat, Near T From US $356
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
Modern Boston Condo | near T From US $535
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace
Historic house renovated for modern convenience From US $460
         

9.8 (134 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
88 Boylston Street · Skyrise Two Stories - Centrally Located From US $436
         

9.6 (41 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Boston Renovation | Near T From US $492
         

9.2 (11 Reviews)
Condo
  • Air Conditioner
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 210+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
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 (1009 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Beautiful 2bd/1.5ba Next to BU 9195 From US $222
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Nice 2bd/1.5ba near BU 6643 From US $302
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
2bd/1.5ba Next to BU 9183 From US $300
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 9837 From US $295
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2BR Next to BU 1884 From US $271
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Gorgeous 2bd/1.5ba Next to BU 4788 From US $266
         

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

Chestnut Hill Varoom and Airbnb Places to Stay Under $200

Over 252+ 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
Sunny,spacious, sleeps 4, steps to MBTA,Hospitals. From US $160
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village From US $190
         

Renovated 2B, In-unit Laundry, Longwood, 1st Flr From US $177
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Sun-filled 1 bed, 1 bath in Brookline Village From US $163
         

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

Instantly Bookable Vacation Homes in Chestnut Hill

Over 352+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Charming Tree Top Victorian - Two Bedroom Retreat From US $403
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Luxury 3brm/1bath Duplex in JP From US $316
         

10.0 (11 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Arbor Retreat From US $371
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sweet House with yard at prime location From US $381
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cozy 1BR Private Unit w/Patio & Parking From US $264
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV
Stylish & Cozy Boston Retreat Near Train Station, Parks & Cafés From US $369
         

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

About Chestnut Hill Vacation Rentals

With more than 681 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Xreservations 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 Xreservations 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 575.39 ft² on average, with prices averaging $334 a night.

Xreservations 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 406
Vacation Homes 175
Hotels with Suites 51
B&B 6
Hostels 4
Others 1

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

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