Photo by Patricia Mari

Sherman Holiday Rentals

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Holiday Rentals in Sherman

Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, 75 reviews
"We had such an awesome stay! Check in process was easy! Amazing scenery amazing adventure we had with our two furr babies!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 62 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
On the beach, sun-loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, 59 reviews
"We had a lovely weekend stay for a quick family get-away. The main kitchen and living area has spectacular views onto the lake as does the deck where we spent most of our time. The lake is just across the very quiet street. The kitchen is incredibly well stocked, the host super responsive and the rooms very comfortable. We did not use the well equipped basement work-out and additional TV space but it looked great. Easy to get to grocery store, hikes, local attractions but honestly we just loved...
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
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Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 29 reviews
"Lovely stay! Comfortable accommodation and welcoming family."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Serenity Awaits at this Cozy Lakeside Bungalow
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, 18 reviews
"Stayed while attending a local wedding and wished we had had more time to hang out at the house! The lake is beautiful and the house had everything we needed! Hope to come back some day!"
Serenity Awaits at this Cozy Lakeside Bungalow
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, 74 reviews
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, 18 reviews
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is HK$3,650
per night
13 Jun - 14 Jun
Lakeview Estate - Chef's Kitchen - NYC Getaway
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 168 reviews
"If you need a relaxing few days in the winter, very good place. Great views and quiet is the key."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 21 reviews
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
9.6 out of 10, Exceptional, 4 reviews
"we were able to have all 3 of our children, with 2 of their spouses and bridal party for my daughter stay with us for the weekend. There were plenty of things to entertain during downtime. Rooms were comfortable and location was convenient to wedding activities."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Peaceful apartment on 3.5 acres w/ artist studio.
Games room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, 11 reviews
"Cute."
The price is HK$1,094
per night
17 Jun - 18 Jun
Peaceful apartment on 3.5 acres w/ artist studio.
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, 8 reviews
"We’d go back."
The price is HK$1,758
per night
12 Jun - 13 Jun
Cozy & Chic Cabin by the Lake, with access to private Beach!
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, 18 reviews
"We had a very pleasant stay! We came for our son’s graduation from West Point. Pat was a gracious host and made sure that we had up to date info. There were lots of thoughtful amenities, the beds and couches were very comfortable, we used the grill and sat on the deck which overlooks a wooded hill. The location is peaceful and in the country just down the street from a horse pasture. You can hear the brook bubbling across the way. The WiFi worked great and although there is just a window air...
The price is HK$1,375
per night
17 Jun - 18 Jun
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Guest Cottage on Country Estate
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, 33 reviews
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, 17 reviews
"The property is lovely and well prepared for guests. The location is wonderful. One of our highlights was watching a bald eagle soar over the lake."
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
Candlewood Lake Retreat with year round views
Property grounds
Candlewood Lake Retreat with year round views
10.0 out of 10, Exceptional, 7 reviews
"We thoroughly enjoyed our time at this wonderful little home. It was pleasantly quiet and secluded, but was just minutes away from some wonderful restaurants and just a short walk to the lake. The hosts were just so responsive and accommodating. We also had one day of rainy weather, which afforded us the opportunity to simply stay in and relax. The kitchen had all of the amenities we could have asked for. The seating area on the deck was spacious and comfortable. We are certainly looking forward...
Candlewood Lake Retreat with year round views
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, 17 reviews
"Gorgeous, as advertised!"
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
The Long View of Candlewood Lake
Smart TV, fireplace
The Long View of Candlewood Lake
9.8 out of 10, Exceptional, 8 reviews
"We were In the area for Kent Graduation . Wish we had more time to spend at the house . Perfect area by lake. Nice setup . Great neighbors . The host was very responsive and so accommodating with our busy schedule and short stay. We’ll be back for a longer stay to enjoy the property, house and lake."
The Long View of Candlewood Lake
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.8 out of 10, Exceptional, 21 reviews
"The property was as described and the living space was perfect for our visit. The deck and views are amazing. If staying at this property, you just need to be aware that it is very difficult getting luggage and groceries into the property. You have to go down a long flight of stairs, walk down a very steep driveway and then go down another flight of stairs. Once you are in, bedroom access requires that you go up or down additional stairs."
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Smart TV, fireplace, ping pong, stereo
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
10.0 out of 10, Exceptional, 11 reviews
"We absolutely loved the house! This was the perfect place to bring my adult children together for a weekend away. The rooms were beautiful, beds were super comfortable, and house nicely decorated. There were spots for smaller groups to sit together and hang out or to come together and chat. The hot tub was appealing to my 20somethings but it was rainy- next time!"
Immaculate waterfront home nestled in the Litchfield hills w/ tons of...
Don't see what you're looking for?
See all available properties in Sherman
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.

Other types of properties in Sherman you may be interested in

Ethan Allen Hotel
Seasonal outdoor pool
Ethan Allen Hotel
3.5 star property
7.8 out of 10, Good, 1,000 reviews
"Wonderful hotel "
The price is HK$990
per night
13 Jun - 14 Jun
Ethan Allen Hotel
Wyndham Southbury
Lobby
Wyndham Southbury
3.0 star property
8.0 out of 10, Very good, 1,010 reviews
"easy check-in and check-out... safe and clean"
The price is HK$857
per night
13 Jun - 14 Jun
Wyndham Southbury
Comfort Inn & Suites Danbury-Bethel
Desk, laptop workspace, iron/ironing board, free WiFi
Comfort Inn & Suites Danbury-Bethel
2.5 star property
8.8 out of 10, Excellent, 126 reviews
"Clean room, comfy bed, microwave in the room, above average free breakfast, pet friendly, our room was quiet, instructions for the tv, larger than average working frig, coffee and water in the lobby, easy parking and lots of restaurants close by. The same basic rate as other similar hotels but includes the amenities that make the difference. "
The price is HK$907
per night
11 Jun - 12 Jun
Comfort Inn & Suites Danbury-Bethel
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.

Search for holiday rentals in Sherman on Expedia! You can easily find your home rentals, villas, holiday apartments in Sherman using one of the methods below:

  • View our selection of featured holiday rentals in Sherman
  • Use the map to find apartments and other holiday homes in the Sherman neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sherman while they last

Look no further and take a look at our great range of rental properties in Sherman!

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?

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. : This holiday home rental outside of Sherman is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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. Squantz Pond State Park and Elephant's Trunk Flea Market are a couple of places you'll find in the wider area.

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.

Recent reviews of Sherman properties
Expedia verified reviews

Rocky River Inn

Rocky River Inn

5/5 Excellent
"Loved our room, everything was renovated!"
A verified traveller stayed at Rocky River Inn
Posted 2 days ago
Rocky River Inn