Skip to content

Vacation rentals in Sherman

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Sherman

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage on Babbling Brook
Entire cabin · 5 guests · 5 beds · 1 bath
Cottage on Babbling BrookCozy, Rustic Cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. A great space for families and friends. Conveniently located on the CT/NY border, just a 1 ½ hour drive or metro north from NYC, the area is a prime location for many reasons. It offers some of the most stunning and scenic drives in the country.
Guesthouse w KAYAKS, BIKES, & passes to LAKE beach
SUPERHOST
Entire guest suite · 4 guests · 3 beds · 1 bath
Guesthouse w KAYAKS, BIKES, & passes to LAKE beachCozy and private studio in attached guest house on 3 bucolic acres w/ pond. Self check-in with private entrance and keypad lock. Newly renovated sleeping loft, kitchen and bath! Enjoy the outdoor deck & patio with grill. Custom post and beam construction inside and natural beauty outside. Year round views of pond, nature trail, and surrounding farms. Mosey or bike along the our scenic country road to the Land Trust. Three miles to quaint town with restaurants, great coffee and town beach.
The Cove Cabin
SUPERHOST
Entire cabin · 6 guests · 2 beds · 1.5 baths
The Cove CabinAn original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Sherman vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Sherman

SUPERHOST
  1. Entire cottage
  2. New Fairfield
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
SUPERHOST
  1. Entire residential home
  2. New Milford
Renovated, one level home in an excellent location
SUPERHOST
  1. Entire cabin
  2. New Fairfield
The Little Lake Cabin - near lake with hot tub
SUPERHOST
  1. Entire residential home
  2. New Fairfield
The Lakeside Nook
SUPERHOST
  1. Entire guesthouse
  2. Gaylordsville
Adorable Cottage in Pastoral Setting
SUPERHOST
  1. Entire rental unit
  2. New Fairfield
Spacious Private Apartment with Stunning Sunsets
SUPERHOST
  1. Entire cottage
  2. Kent
Perfection in Litchfield County, 4 BR with Pool
  1. Entire cottage
  2. US
Little Put Cottage (Brewster, NY)
SUPERHOST
  1. Entire residential home
  2. New Fairfield
Lake View Retreat from the Big City
  1. Entire cottage
  2. Kent
Pond cottage for rent- October & November
SUPERHOST
  1. Entire residential home
  2. Wingdale
Renovated Milk House on Gorgeous Working Farm
SUPERHOST
  1. Entire cottage
  2. New Milford
BUNTING HOUSE : CANDLEWOOD LAKEFRONT! 3BR CHALET