A person standing on a dock extending into a calm lake, surrounded by dense forested hills under a clear sky.

Sherman Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Sherman holiday rentals

A rustic cabin surrounded by a forest with a stream in the foreground.

1. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is AU$921
includes taxes & fees
28 Oct - 29 Oct
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A neatly made bed with a white textured bedspread, two bedside lamps, a small bedside table with a vase, and a basket with a photo frame.

2. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
United States
Jim B.
The price is AU$210
includes taxes & fees
3 Nov - 4 Nov
Cozy private room in a shared home with a Full-size bed and private bathroom.
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

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

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is AU$464
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

4. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
10.0 out of 10, Exceptional, (1 review)
"Perfect!!"
United States
Jeni O.
The price is AU$1,228
includes taxes & fees
26 Oct - 27 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

5. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (5 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is AU$773
includes taxes & fees
20 Oct - 21 Oct
The Little Lake Cabin with hot tub
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

6. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$819
includes taxes & fees
21 Oct - 22 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A living room with a fireplace, two armchairs, a sofa, and a TV.

7. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is AU$364
includes taxes & fees
29 Oct - 30 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

8. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful experience! The RV was very nice and cozy. Everything was clean and well maintained. The property was beautiful. The host was very helpful and accommodating. Definitely plan on coming back!"
United States
Fernanda
The price is AU$268
includes taxes & fees
18 Oct - 19 Oct
Welcome to Sweet Abby Rose!
A hot tub in a backyard with a house, trees, and a clear sky.

9. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AU$5,046
includes taxes & fees
18 Oct - 19 Oct
Las Flores Villa
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

10. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$346
includes taxes & fees
28 Oct - 29 Oct
The Perch in the Purchase -- Cozy, unique, and private
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

11. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AU$527
includes taxes & fees
3 Nov - 4 Nov
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A white house with a wooden staircase leading to a porch.

12. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is AU$203
includes taxes & fees
18 Oct - 19 Oct
Cozy One Bedroom Apartment Centrally Located in Southbury
A wooden deck with a lounge chair and a table, a small wooden house with a door and windows, and a wooden fence.

13. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.0 out of 10, Wonderful, (13 reviews)
"Perfect little getaway, adorable space and wonderfully accommodating hosts."
United States
Susan
The price is AU$359
includes taxes & fees
22 Oct - 23 Oct
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
A vending machine with various snacks and drinks.

14. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
The price is AU$190
includes taxes & fees
18 Oct - 19 Oct
1 King Bed | Non-Smoking
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

15. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (5 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is AU$734
includes taxes & fees
2 Nov - 3 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

16. The Overlook near South Farms in Litchfield County is Hospitality, integrated.

The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris
9.8 out of 10, Exceptional, (19 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$392
includes taxes & fees
18 Oct - 19 Oct
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

17. Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.4 out of 10, Very good, (12 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
The price is AU$202
includes taxes & fees
16 Nov - 17 Nov
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

18. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is AU$399
includes taxes & fees
18 Oct - 19 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A white house with a steeply pitched roof and a small tower-like structure.

19. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (8 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is AU$693
includes taxes & fees
18 Oct - 19 Oct
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

20. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is AU$888
includes taxes & fees
11 Nov - 12 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
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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Top Sherman Hotel Reviews

La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

10/10 Excellent
"Breakfast was good. The room was very clean."
Anish 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Danbury

Find out more about Sherman

Everything you need to know about Sherman holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sherman holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sherman holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sherman holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sherman holiday rentals we have selected for you start as low as AU$268 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sherman rentals

At Expedia, we put the best Sherman holiday 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 holiday.

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 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, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Sherman offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Sherman?

With 9 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.