Romantic Wine Tours - Vacation Rentals in Chestnut Hill

Modern NEW Luxury Townhouse - 1 mile to Downtown & Broadway From US $333
         

Market Street House by Stay Local Nashville From US $287
         

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10.0 (2 Reviews)
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Chic Charming Private Home - Enjoy a unique Nashville. From US $249
         

9.0 (221 Reviews)
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  • Pet Friendly
Downtown Luxury Victorian From US $333
         

10.0 (224 Reviews)
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Luxury Nashville 5 Stars Home 1.3m From Broadway! From US $315
         

Hot Tubs + Rooftops | Sleeps 20 Near Broadway From US $1,451
         

10.0 (16 Reviews)
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Luxury Places to Stay in Chestnut Hill

Over 136+ Luxury Places to Stay in or Near Chestnut Hill
The Elmwood & Ashford - 8BR WeHo Rooftops From US $1,874
         

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The Chestnut + Linden | 8 BR, Skyline Views From US $1,478
         

10.0 (1 Review)
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The Taylor Martin by Stay Local Nashville From US $1,369
         

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Pet-Friendly Vacation Rentals in Chestnut Hill

Over 82+ Pet-Friendly Vacation Rentals in or Near Chestnut Hill
Hart Suite 14 by AvantStay | Gorgeous Town House w/Modern Amenities! From US $365
         

The Hart Suites by AvantStay From US $462
         

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8.8 (3 Reviews)
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10min to Broadway/DT | 6BR (2 homes) | Hart Suites From US $780
         

10.0 (1 Review)
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Pet friendly, 5 Min to Downtown, gated parking From US $306
         

9.8 (28 Reviews)
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Large Vacation Homes & Villas in Chestnut Hill

Over 52+ Large Vacation Homes & Villas in or Near Chestnut Hill
The Martin - Modern Home with Rooftop Deck From US $633
         

10.0 (1 Review)
Condo
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The Taylor From US $637
         

9.8 (9 Reviews)
Condo
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Rooftop Views & Hot Tub Near Downtown From US $474
         

9.6 (18 Reviews)
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Luxury Downtown Nashville Rooftop Deck 11 Beds From US $571
         

9.6 (15 Reviews)
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Hart Suite Buyout 6 by AvantStay | Two Nashville Town Houses From US $707
         

Wheelchair Accessible Vacation Homes in Chestnut Hill

Over 13+ Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Harthall Hotel From US $250
         

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8.6 (721 Reviews)
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Harthall Hotel From US $144
         

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8.4 (79 Reviews)
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Sonder The Retreat | Superior Three-Bedroom Apartment w/Rooftop From US $216
         

9.2 (28 Reviews)
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  • Wheelchair Accessible
Sonder The Retreat | Three-Bedroom Apartment w/Rooftop From US $385
         

9.0 (40 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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

Over 10+ Chestnut Hill Vacation Rentals and Airbnb Places to Stay Under $200
Urban Art District Abode From US $188
         

6.0 (1 Review)
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Charming 2-bedroom in heart of Wedgewood Houston From US $115
         

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The Record House near the Heart of Music City From US $101
         

10.0 (1 Review)
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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 55+ Instantly Bookable Vacation Homes in or Near Chestnut Hill
Market Street House - Enchanted Victorian From US $535
         

10.0 (3 Reviews)
House
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  • Balcony/Terrace
Chic 3BDR Townhome in Music City | Hart Suites From US $377
         

9.4 (98 Reviews)
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  • Pet Friendly
Trendy WeHo Home | Near DT Nashville! From US $455
         

9.2 (51 Reviews)
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Hart Suite Buyout 2 by AvantStay | Two Nashville Town Houses From US $723
         

Lovely ADULTS ONLY XXX studio in vibrant Nashville From US $231
         

About Chestnut Hill Vacation Rentals

With more than 145 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Romanticwinetours 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 Romanticwinetours 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 6469.45 ft² on average, with prices averaging $721 a night.

Romanticwinetours 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 76
Holiday Apartments 37
B&B 6
Cottages 6
Villas 2
Hotels with Suites 1

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

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

What are the top vacation rentals in Chestnut Hill?
Which vacation homes in Chestnut Hill are best for families?

If you are looking for a family-friendly vacation home in Chestnut Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestnut Hill:

How many vacation rentals are available in Chestnut Hill?

Currently, the total number of properties listed in 2026 is over 145 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.