Winters Vacations Rentals - Vacation Rentals in The Driving Range

The Meadows at Kimstead Farm From US $355
         

10.0 (15 Reviews)
House
  • Air Conditioner
  • TV
  • View
Paddlers Paradise on Hickory Hills Lake! From US $442
         

10.0 (1 Review)
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Howarth House B&B From US $235
         

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10.0 (112 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Modern 3BR Near FSU 15 Min to Wachusett From US $242
         

10.0 (14 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Maguire House Bed and Breakfast From US $225
         

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10.0 (9 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
The Maguire House Bed & Breakfast From US $262
         

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10.0 (36 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cottage beside a waterfall From US $290
         

10.0 (12 Reviews)
Cottage
  • Parking
  • Security/Safety
  • Bedding/Linens
Modern 3BR Near FSU - 15 Min to Wachusett From US $199
         

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10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
The Birchwood Inn From US $190
         

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9.4 (227 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cabin & Sauna on Lake Monomonac near Mt. Monadnock From US $269
         

10.0 (12 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Waterfront Gem w/Dock on Lake Monomonac From US $310
         

A Quintessential New England Historical Guesthouse From US $1,640
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Child Friendly
Fitchburg quiet side modern 2BD. From US $236
         

10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
River Room overlooking the waterfall From US $288
         

10.0 (3 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Cabin & Sauna on Lake Monomonac near Mt. Monadnock From US $335
         

Unique Cozy private 1-bedroom apartment in charming Temple From US $380
         

Quiet private pond getaway From US $272
         

9.6 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
2 queen and 2 twin beds From US $247
         

9.6 (15 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Mid-Century Comfort & Style From US $254
         

9.6 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals 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 The Driving Range.

Weather in The Driving Range

View the weather forecast for The Driving Range before booking your The Driving Range 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

The Driving Range Vacation Rental Frequently Asked Questions

What are the top vacation rentals in The Driving Range?
How many vacation rentals are available in The Driving Range?

Currently, the total number of properties listed in 2026 is over 143 in the The Driving Range area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Driving Range.