24+ Vacation Rentals Near Holly Ridge Winery |
  1. USA
  2. Tennessee
  3. Cookeville
  4. Holly Ridge Winery

Montgomery Cottages - Vacation Rentals in Holly Ridge Winery

Talley's Cabins By Dale Hollow Lake. Right Where You Want To Be! From US $157
         

10.0 (105 Reviews)
Cabin
Talley's Cabins By Dale Hollow Lake. Right Where You Want To Be!
  • Air Conditioner
  • Parking
  • TV

View Availability
Overton Motel From US $55
         

|
6.1 (86 Reviews)
Hotel
Overton Motel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

View Availability
Overton Motel Livingston From US $62
         

6.6 (210 Reviews)
Hotel
Overton Motel Livingston
  • Air Conditioner
  • Parking
  • Designated Smoking Area

View Availability
Historic Loft with balconies. From US $102
         

10.0 (12 Reviews)
Apartment
Historic Loft with balconies.
  • Air Conditioner
  • TV
  • Security/Safety

View Availability
Downtown 4-bedroom with boat and Rv parking close to Lake From US $345
         

10.0 (10 Reviews)
House
Downtown 4-bedroom with boat and Rv parking close to Lake
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
2 bdrm 3bath downtown apartment From US $340
         

10.0 (4 Reviews)
Apartment
2 bdrm 3bath downtown apartment
  • Air Conditioner
  • Parking
  • TV

View Availability
2-bedroom house in peaceful Hilham with WiFi, AC From US $171
         

10.0 (4 Reviews)
House
2-bedroom house in peaceful Hilham with WiFi, AC
  • Air Conditioner
  • Parking
  • TV

View Availability
Speakeasy-2 bedroom/2 bath- on the Downtown Square From US $189
         

10.0 (1 Review)
House
Speakeasy-2 bedroom/2 bath- on the Downtown Square
  • Security/Safety
  • Child Friendly

View Availability
Charming 1-bedroom traditional apartment in enchanting Livingston. From US $188
         

10.0 (1 Review)
Apartment
Charming 1-bedroom traditional apartment in enchanting Livingston.
  • Air Conditioner
  • Parking
  • TV

View Availability
The Mason Apartment-Cozy Getaway From US $136
         

10.0 (1 Review)
House
The Mason Apartment-Cozy Getaway
  • Air Conditioner
  • Parking
  • TV

View Availability
Campers Travelers Nurses. From US $93
         

6.8 (5 Reviews)
RV Rental
Campers Travelers Nurses.
  • Air Conditioner
  • Security/Safety
  • Internet

View Availability
Gorgeous Home in the Heart of Historic Downtown From US $236
         

New
House
Gorgeous Home in the Heart of Historic Downtown
  • Air Conditioner
  • Parking
  • TV

View Availability
The Cullom-2BR Gem in the Heart of Town From US $161
         

New
Apartment
The Cullom-2BR Gem in the Heart of Town
  • Air Conditioner
  • Parking
  • TV

View Availability
The Miller on the Livingston Square! From US $155
         

New
House
The Miller on the Livingston Square!
  • Air Conditioner
  • Parking
  • TV

View Availability
The Officer-Chic 1 bedroom on the Historic Square From US $137
         

New
House
The Officer-Chic 1 bedroom on the Historic Square
  • Air Conditioner
  • Parking
  • TV

View Availability
Historic Downtown Suite — Steps from Dining & Shopping From US $132
         

New
Apartment
Historic Downtown Suite — Steps from Dining & Shopping
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
The Callie- Downtown by the square & park. Tons of Parking. On 3 Acres! From US $214
         

10.0 (11 Reviews)
House
The Callie- Downtown by the square & park. Tons of Parking. On 3 Acres!
  • Air Conditioner
  • Parking
  • TV

View Availability
The Bella Vita- downtown by the square & park From US $299
         

10.0 (3 Reviews)
House
The Bella Vita- downtown by the square & park
  • Air Conditioner
  • Parking
  • TV

View Availability
The Posh- Downtown by the square & park From US $135
         

9.8 (14 Reviews)
House
The Posh- Downtown by the square & park
  • Air Conditioner
  • Parking
  • TV

View Availability
Farmhouse in Livingston From US $132
         

10.0 (27 Reviews)
Other
Farmhouse in Livingston
  • Air Conditioner
  • Parking
  • TV

View Availability
Private apartment in the completely restored & oldest Livingston Sq building. From US $188
         

10.0 (4 Reviews)
Apartment
Private apartment in the completely restored & oldest Livingston Sq building.
  • Air Conditioner
  • Parking
  • TV

View Availability
Flatt Creek Cottage in Livingston From US $205
         

10.0 (1 Review)
House
Flatt Creek Cottage in Livingston
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Culper Retreat- Charming 2-bedroom house in welcoming Cookeville with WiFi, AC From US $222
         

New
House
Culper Retreat- Charming 2-bedroom house in welcoming Cookeville with WiFi, AC
  • Air Conditioner
  • Parking
  • TV

View Availability
Private Apartment in beautifully restored building on The Livingston Square. From US $130
         

New
Apartment
Private Apartment in beautifully restored building on The Livingston Square.
  • Air Conditioner
  • Parking
  • TV

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

Weather in Holly Ridge Winery

View the weather forecast for Holly Ridge Winery before booking your Holly Ridge Winery 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

Top Attractions Around Holly Ridge Winery, TN

Montgomerycottages offers a large selection of top attractions around Holly Ridge Winery. Research things to do on your vacation before you visit Holly Ridge Winery.


Tennessee Tech University Cummins Falls State Park Dale Hollow Reservoir Center Hill Lake Dale Hollow Lake State Resort Park Golf Course Edgar Evins State Park Burgess Falls State Park Mountain View Park Golden Eagle Golf Club Cookeville History Museum Standing Stone State Park Standing Stone Hidden Valley Golf and Country Club Dogwood Park Cookeville Depot Museum Cane Creek Park Overton County Heritage Museum White Plains Golf Course Cookeville Performing Arts Center Rainbow Guide Service

Holly Ridge Winery Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Holly Ridge Winery?

Currently, the total number of properties listed in 2026 is over 24 in the Holly Ridge Winery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Holly Ridge Winery.