Owner Direct Vacation Rentals in Chestnut Hill

The Best Owner Direct Vacation Rentals in Chestnut Hill. Explore thousands of vacation home rentals, large cabins, and villas near Chestnut Hill

Songbird Suite AB From US $774
         

New
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Harthall Hotel From US $132
         

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8.4 (39 Reviews)
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  • Pet Friendly
Songbird Suite A From US $586
         

New
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Chic Charming Private Home - Enjoy a unique Nashville. From US $204
         

9.0 (212 Reviews)
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  • Pet Friendly
Trendy WeHo Home - Near DT Nashville From US $539
         

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New
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Downtown Luxury Victorian From US $320
         

10.0 (221 Reviews)
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Songbird Suite B From US $493
         

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New
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Luxury Places to Stay in Chestnut Hill

Over 118+ Luxury Places to Stay in or Near Chestnut Hill
Hot Tubs + Rooftops | Sleeps 20 Near Broadway From US $831
         

10.0 (12 Reviews)
House
  • Air Conditioner
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  • Pet Friendly
The Ashford - Brand New Gem, Walk to WeHo! From US $779
         

Pet-Friendly Vacation Rentals in Chestnut Hill

Over 65+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
Hart Suites by AvantStay – Stylish Townhome Near Downtown Nashville From US $462
         

The Elmwood - Brand New, Rooftop Lounge w Firepit From US $644
         

10.0 (1 Review)
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  • Pet Friendly

Large Vacation Homes & Villas in Chestnut Hill

Over 38+ Large Vacation Homes & Villas in or Near Chestnut Hill
The Ashford - Brand New Gem Walk to WeHo From US $443
         

The Chestnut - Brand New Rooftop Skyline Views From US $443
         

10min to DT | 3BR Home w/Bunk Rooms | Hart Suites From US $378
         

Rooftop Views & Hot Tub Near Downtown From US $410
         

9.6 (17 Reviews)
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 13+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Oasis on 2nd #201 From US $531
         

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New
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Sonder The Retreat From US $919
         

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8.6 (30 Reviews)
Apartment
  • Air Conditioner
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  • Wheelchair Accessible
Harthall Hotel From US $178
         

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8.7 (766 Reviews)
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  • Pet Friendly
Oasis on 2nd #301 From US $568
         

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10.0 (1 Review)
Apartment
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  • Wheelchair Accessible
  • Balcony/Terrace
Sonder The Retreat | Superior Three-Bedroom Apartment w/Rooftop From US $216
         

9.2 (28 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Chestnut Hill Varoom and Airbnb Places to Stay Under $200

Over 10+ Chestnut Hill Varoom and Airbnb Places to Stay Under $200
Charming 2-bedroom in heart of Wedgewood Houston From US $115
         

New
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  • Pet Friendly
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The Record House near the Heart of Music City From US $101
         

10.0 (1 Review)
Apartment
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  • Security/Safety
Luxury Escape at on 2nd Ave From US $189
         

4.5 (8 Reviews)
House
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  • Pet Friendly
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Instantly Bookable Vacation Homes in Chestnut Hill

Over 54+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Lovely ADULTS ONLY XXX studio in vibrant Nashville From US $233
         

Chic 3BDR Townhome in Music City | Hart Suites From US $351
         

Boutique Hotel Vibes + 3 Kings + Walkable Neighborhood From US $522
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Trendy WeHo Home | Near DT Nashville! From US $344
         

9.2 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Luxury + Hot Tub | Near Broadway From US $424
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Taylor - Modern Space with Stunning Rooftop From US $527
         

The Martin - Modern Home with Rooftop Deck From US $527
         

About Chestnut Hill Vacation Rentals

With more than 127 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect 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 Ownerdirect 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 5669.72 ft² on average, with prices averaging $468 a night.

Ownerdirect 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
Vacation Homes 71
Holiday Apartments 34
Cottages 7
Villas 2
Hotels with Suites 1

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

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