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Sherman Holiday Rentals

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Holiday Rentals in Sherman

Serene Hudson Valley Escape w/ Pool & Grill

Serene Hudson Valley Escape w/ Pool & Grill

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.2 out of 10, Wonderful, (15)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (35)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Magnificent Lake View

2.0 star property
Magnificent Lake View

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (82)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (121)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is NZ$1,011
includes taxes & fees
17 July - 18 July
Hickory on Willow Lake

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very good, (7)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm

Spectacular Lake front house

9.6 out of 10, Exceptional, (4)
"This beautiful home offered plenty of space for our family of 6 adults and 2 children to enjoy a week together. "
Spectacular Lake front house

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very good, (1)
"We rented this place for the first time for a family gathering. The setting was very private and “country-ish”. For the most part everything listed was present at the place and there were enough sleeping options for our crew. Overall - the owners were nice and fairly responsive but there was a level of disappointment to the care of the property and more importantly the preparedness for our arrival. They said the pool and hot tub were cleaned and ready but the pool was still dirty and the hot tub...
Spacious Woodbury Home w/ Pool + Hot Tub!

New One Bedroom Apartment Centrally Located in Southbury

9.8 out of 10, Exceptional, (6)
"Excellent place in an excellent location. Charles is a wonderful host. Will be staying there again. "
The price is NZ$263
includes taxes & fees
8 Aug - 9 Aug
New One Bedroom Apartment Centrally Located in Southbury

Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

10.0 out of 10, Exceptional, (10)
"We had some trouble with our check in process, but the response time to fix it was quick. The hot tub was lovely, and the pool house was so fun for both the adults and the kids. There was an issue with my wife finding old kids applesauce packets behind the couch throw pillow. Other than that it was a great stay. Kids had fun on the swings and hammock."
Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

10.0 out of 10, Exceptional, (79)
"We stayed for a birthday weekend with a few other couples and had a great time. There is plenty of space for everyone to spread out and each 'area' of the house is incredibly comfortable (especially the movie theater). If you need anything there are plenty of stores close by and the area is very safe. Overall, no complaints and would recommend to anyone looking for a getaway."
Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

My favorite place!

2.0 star property
2.0 out of 10, (1)
My favorite place!

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"This is a beautiful home even if you live in the area and just want to spend the weekend at the lake, it’s a perfect getaway. We love that it was dog friendly. The host was wonderful and very accommodating. The house came stocked with everything that you would need for a perfect stay. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (42)
"Had an amazing stay. House was stocked with all of the essentials. Fantastic location. Would definitely stay again!"
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (86)
"We had an amazing time. The house was beautiful and clean and communication between us and the hosts was wonderful. We would love to stay there again!"
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find a holiday rental in Sherman?

Yes, there are holiday rentals close to the most popular sights in Sherman, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Sherman has to offer?

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!: This holiday home rental outside of Sherman is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Sherman?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Sherman stay.

What’s there to see and do in Sherman?

Candlewood Lake and Housatonic River are a couple of lovely local spots to get outside and enjoy nature. While here, Town Meadows and Mildred Strauss and James Morrissey Family Nature Preserves are other places worth a visit.

What’s a holiday rental in Sherman like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sherman. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.