Photo by Patricia Mari

Holiday Rentals in Sherman

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Holiday Rentals in Sherman

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

9.2 out of 10, Wonderful, (33)
"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

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

10.0 out of 10, Exceptional, (76)
"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.

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

9.4 out of 10, Exceptional, (88)
"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!

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Litchfield Hills Hideaway

10.0 out of 10, Exceptional, (55)
"Great place to end our Gilmore Girls adventure!!! The Hideaway was clean and cozy, and the hosts are very professional! We would stay here again!!!!"
The price is €239
includes taxes & fees
23 Apr - 24 Apr
Litchfield Hills Hideaway

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (8)
"The house had room for all of us, spacious and comfortable with modern amenities. We enjoyed the large open kitchen, well equipped for making big meals, and especially loved the walk in pantry with sink, oven and coffee bar. The beds were comfy, the bathrooms deluxe. Large couch and huge TV in living room with cozy gas fireplace for us to gather and relax. Located on a quiet cul de sac, easy to get to local attractions. We enjoyed every minute of our stay."
The price is €862
includes taxes & fees
1 May - 2 May
Spacious New Luxurious holiday house in lovely Hudson Valley

Cozy Cabin @ Sticks & Stones Farm

8.8 out of 10, Excellent, (3)
"Nice clean cabin. Good communication with host."
The price is €180
includes taxes & fees
21 Apr - 22 Apr
Cozy Cabin @ Sticks & Stones Farm

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

9.6 out of 10, Exceptional, (24)
"We made happy memories over a cold January weekend. We cooked together, sat around the fire, played games and dozed in comfortable beds with high quality linens. We enjoyed the view of the water and the twinkling lights on the property at night. The steam shower was divine. If you like cooking, bring good knives, a veggie peeler and good pans. Plenty of glassware and dishes and some cookware provided. "
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (23)
"Very cute , well supplied, clean, nice property. Wed definitely stay again. 1"
Cozy & Chic Cabin by the Lake, with access to private Beach!

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

9.6 out of 10, Exceptional, (5)
"The house on the lake is clean and very cute. A few things to keep in mind… The stairs to the loft are VERY steep and VERY narrow. So both adults and small children may struggle to get up and down, especially with any type of luggage. There are no closets or dressers for your clothes so maybe bring hangers and a hook for behind the door. Everything else was perfect. "
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (33)
"Great place. Really enjoyed staying there"
The Goshen Glass Chalet

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.2 out of 10, Wonderful, (20)
"The best part of the stay was fun with family because of the mini pool table/air hockey and darts. Kids loved it! "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Peaceful apartment on 3.5 acres w/ artist studio.

9.8 out of 10, Exceptional, (15)
"This adorable cottage attached to the main house was fabulous for my wife and I for 4 nights! It has a little kitchen, space heaters everywhere (us southerners can’t handle the New England winters like we used to!) and was very clean! We have never stayed in an attached rental before and I would say we would be open to exploring more because of our experience! "
The price is €195
includes taxes & fees
15 Apr - 16 Apr
Peaceful apartment on 3.5 acres w/ artist studio.

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (14)
"We visited here for my wife’s birthday with friends. Great location, while it’s just a 2 hour drive from the city the property is has a great location with its own privacy and wonderful light lit living room. The place is well stocked with utensils and linens. Host was very responsive and kind.Thank you for creating the wonderful time for us"
Hidden Charm in Hudson Valley In Dutchess County

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

9.6 out of 10, Exceptional, (84)
"My girlfriends and mine were looking for a nice weekend getaway to unwind. The property was very clean. The basement level seemed a little more disheveled than pictured and very cold. Unfortunately we didn’t spend any time down there. The rest of the property was wonderful and spotless! Beds were comfortable."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

10.0 out of 10, Exceptional, (39)
"Excellent stay in s as wonderful house. "
Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

10.0 out of 10, Exceptional, (12)
"Great place to stay for all ages. Had everything we needed and lots of room to relax. Definitely will stay here again next time we come. Comfy beds, easy to get to, easy check in, everything we needed in the kitchen, lots of books and toys, great outdoor space. Thanks for providing the perfect place to stay with extended family! "
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

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

9.6 out of 10, Exceptional, (11)
"I was pleasantly surprised! The house looked even better in person than it did in the photos. It is warm and comfortable and they had everything we needed to enjoy our time away. The house was clean and the surrounding property was well maintained. I would love to come back in the spring/summer to enjoy more of the outdoors. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakefront Spring Stunner in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (68)
"Charming cottage with beautiful lake views. It’s clean and stocked with things like coffee and spices, so you don’t need to buy a lot of extra things just for a short stay. Lots of wildlife and convenient for both short and extensive walks/hikes. "
Lakefront Spring Stunner in New England Just 2 Hours From NYC
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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Other types of properties in Sherman you may be interested in

Hotel Zero Degrees Danbury

4.0 star property
9.0 out of 10, Wonderful, (1002)
"It was great!!"
The price is €166
includes taxes & fees
19 Apr - 20 Apr
Hotel Zero Degrees Danbury

Ethan Allen Hotel

3.5 star property
7.8 out of 10, Good, (1006)
"Well appointed"
The price is €106
includes taxes & fees
21 Apr - 22 Apr
Ethan Allen Hotel

Wyndham Southbury

3.0 star property
8.0 out of 10, Very good, (1001)
"The girl and the dust was awesome. She was quick very courtesy. The rooms were nice and clean. The lobby was clean the nice and yes, I will stay there again."
The price is €88
includes taxes & fees
21 Apr - 22 Apr
Wyndham Southbury
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.

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?

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views: This holiday home rental outside of Sherman is located in the mountains, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family.

How many holiday rentals are there in Sherman?

With 7 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.