Photo by Patricia Mari

Sherman Vacation Rentals

Vacation Rentals in Sherman

On the beach, sun loungers
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
9.6 out of 10, Exceptional, (58)
"Property manager was very kind and responsive. Greatly enjoyed the views of the pond and the basement pool and ping pong tables. Great time playing these games with mybson as the weather wasn't conducive for water activities."
Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond
Beach nearby, beach towels
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
9.4 out of 10, Exceptional, (75)
"Thoroughly enjoyed our stay at Squantz Cottage. Property was well maintained, clean, and convenient. Parking at the cottage can be a little tricky backing out and getting on to the road. An option to park at the main house could be helpful. I would definitely rent again!"
Lake Cottage 3 Private Beaches w/ Kayaks, 1 hour & 15 Minutes from NYC
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (16)
"We really enjoyed staying at this cottage, much better than 2 rooms in a hotel. Very quiet, fully equipped kitchen.Easy to prepare meals when we wished. We visit the Ridgefield area several times per year and will definitely consider staying here again."
Serenity Awaits at this Cozy Lakeside Bungalow
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Game room
Peaceful apartment on 3.5 acres w/ artist studio.
10.0 out of 10, Exceptional, (11)
"Cute."
The price is $140
$213 total
includes taxes & fees
May 28 - May 29
Peaceful apartment on 3.5 acres w/ artist studio.
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, (28)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"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
Property grounds
Tranquil Lakefront Cottage - Private Dock, Kayaks, Stunning Views, Family Friendly
10.0 out of 10, Exceptional, (17)
"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
Property grounds
Lakefront New York Abode w/ Deck, Grill & Fire Pit
10.0 out of 10, Exceptional, (3)
"Clean, spacious, and many activities in a nice quiet town. The house comfortably fit our 10 people."
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Dining
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
7.0 out of 10, Good, (4)
"Oven and stove top very dirty , SPA pool water not clean,no washer and dryer"
The price is $399
$593 total
includes taxes & fees
May 27 - May 28
@iHeartNYState 4BR. Hot Tub Jacuzzi Fireplace
Property grounds
Lake Luxury
10.0 out of 10, Exceptional, (8)
"We loved our stay at this home. Plenty of space so we didn’t feel like we were on top of each other, gorgeous kitchen (plus a separate butler’s kitchen!), and lux bathrooms made this rental exactly what we needed. Thanks Gianna!"
Lake Luxury
Property grounds
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
10.0 out of 10, Exceptional, (16)
"What a beautiful home with a spectacular view. We had the most relaxing, fun filled vacation!! The amenities were over and beyond what any of us ever expected."
Beautiful Renovated 2BR 2B Direct Waterfront Candlewood Lake Home~Sunset Views!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (7)
"Absolutely loved my stay. The host was incredibly accommodating and went above and beyond to make sure we had everything we needed. The space was stylish, clean, and cozy, with thoughtful touches throughout. The location was perfect, close to all the attractions yet tucked away in a quiet neighborhood. Would highly recommend to anyone looking for a comfortable and enjoyable stay!"
The price is $200
$426 total
includes taxes & fees
May 28 - May 29
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Property grounds
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
10.0 out of 10, Exceptional, (6)
"This was a great location. Only changes I would make is a light under the eagle to find it better at night and to update the listing with the new photo of house with the blue paint."
Waterfront Luxury Lakehouse w/ Boat Dock & Kayaks. Priceless Views & Amenities.
Smart TV, fireplace
The Long View of Candlewood Lake
10.0 out of 10, Exceptional, (6)
"It was such a nice property and the host was amazing"
The Long View of Candlewood Lake
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (32)
"Staying at Kerry’s was a dream! It was our family’s first Christmas without my dad. My moms wish was to have her children and grand children together in one place for the holiday. From the moment I reached out to Kerry I knew we had chosen the right place. She was incredibly kind and accommodating. The property and the views were stunning and immaculate. The house had everything we needed and more…I was surprised to find a beautiful Christmas tree upon arrival - making it feel like home away...
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor pool
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
10.0 out of 10, Exceptional, (17)
"House is very cute. The scenery in early spring was amazing. Very quiet neighborhood. Conveniently located. Very clean. Beds were very comfortable. Had everything we needed."
The price is $157
$295 total
includes taxes & fees
May 28 - May 29
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
Property grounds
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
9.6 out of 10, Exceptional, (20)
"We came for a girls weekend. The house is beautiful with plenty of comfy seating. Super clean. The view is beautiful and fun to watch all the boaters. We could not get fire pit to work, but this could have been user error. I would caution others that the stairs are a lot! Definitely not for elders and a real workout, but this was clearly stated in description. Otherwise an absolute dream house with plenty of space. The attention to detail and decor (especially in the bathrooms) was appreciated!...
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (18)
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
The price is $356
$813 total
includes taxes & fees
May 27 - May 28
Lakeview Estate - Chef's Kitchen - NYC Getaway
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (21)
"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
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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

Seasonal outdoor pool
Ethan Allen Hotel
3.5 star property
7.8 out of 10, Good, (1001)
"Very comfortable and clean hotel in Danbury. We have stayed before due to family in the area. The rooms are clean and comfortable and the staff is very accommodating."
The price is $115
$133 total
includes taxes & fees
May 27 - May 28
Ethan Allen Hotel
Lobby
Wyndham Southbury
3.0 star property
8.0 out of 10, Very Good, (1005)
","
The price is $101
$116 total
includes taxes & fees
May 27 - May 28
Wyndham Southbury
Standard Room, 2 Queen Beds, Non Smoking | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels
Comfort Inn & Suites Danbury-Bethel
2.5 star property
9.0 out of 10, Wonderful, (105)
"They live up to their standards, and they are quick to respond if something needs their attention."
The price is $115
$132 total
includes taxes & fees
Jun 2 - Jun 3
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.

Everything you need to know about Sherman vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sherman vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sherman vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sherman vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sherman. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sherman in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sherman rentals

At Expedia, we put the best Sherman vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sherman rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sherman vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sherman. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Sherman?

Yes, we offer vacation rentals near top local attractions in Sherman, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Sherman?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: Visitors like this Sherman vacation home rental. It is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

How many vacation rentals are there in Sherman?

With 8 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Sherman like?

A vacation rental is a private property you can stay in for a couple of days or more in Sherman. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.

Recent reviews of Sherman properties
Expedia verified reviews

Microtel Inn & Suites by Wyndham Bethel/Danbury

Microtel Inn & Suites by Wyndham Bethel/Danbury

5/5 Excellent
"We have been to a lot of pet friendly hotels. This one impressed with cleanliness"
A verified traveler stayed at Microtel Inn & Suites by Wyndham Bethel/Danbury
Posted 13 hours ago
Microtel Inn & Suites by Wyndham Bethel/Danbury