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

Sherman Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Sherman vacation 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.
$490 nightly
The price is $555
Oct 7 - Oct 8
Total with taxes and fees
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
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.

2. 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.
$301 nightly
The price is $341
Oct 18 - Oct 19
Total with taxes and fees
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

3. 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, (2 reviews)
"Clean and close to activitys"
United States
randall
$137 nightly
The price is $155
Oct 13 - Oct 14
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
$187 nightly
The price is $212
Oct 6 - Oct 7
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

5. "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.
$511 nightly
The price is $578
Oct 13 - Oct 14
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

6. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
$170 nightly
The price is $184
Oct 6 - Oct 7
Total with taxes and fees
Welcome to Sweet Abby Rose!
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

7. 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
$706 nightly
The price is $802
Oct 6 - Oct 7
Total with taxes and fees
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern kitchen with a dining area, large windows, and a TV displaying a streaming service.

8. 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, (5 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$204 nightly
The price is $231
Oct 18 - Oct 19
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
A multi-story house with a dock and boats, surrounded by dense forest.

9. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed the property. Beautiful house. Great location. Reserve, stay and enjoy!"
United States
Ron P.
$1,061 nightly
The price is $1,203
Oct 14 - Oct 15
Total with taxes and fees
North Cliff House - Private Dock & Sauna
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

10. 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.
$344 nightly
The price is $373
Nov 3 - Nov 4
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A hotel room with two beds, a desk, a chair, and a TV.

11. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Bethel
$120 nightly
The price is $137
Oct 6 - Oct 7
Total with taxes and fees
2 Queen Beds | Non-Smoking
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.
$106 nightly
The price is $118
Oct 20 - Oct 21
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

13. 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.
$247 nightly
The price is $279
Oct 6 - Oct 7
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

14. 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, (18 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$245 nightly
The price is $277
Oct 6 - Oct 7
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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.
$500 nightly
The price is $566
Nov 2 - Nov 3
Total with taxes and fees
Escape to Bantam Lake- With Fireplace and Hot tub!
A vending machine with various snacks and drinks.

16. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Bethel
$115 nightly
The price is $132
Oct 6 - Oct 7
Total with taxes and fees
1 King Bed | Non-Smoking
A view through a window with a clear sky and lush greenery outside.

17. Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$261 nightly
The price is $295
Nov 2 - Nov 3
Total with taxes and fees
Private Apartment in Southbury 101
A modern hotel room with a large bed, a desk with a chair, a flat-screen TV, and a window with curtains.

18. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Bethel
$110 nightly
The price is $126
Oct 6 - Oct 7
Total with taxes and fees
1 Queen Bed | Non-Smoking
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

19. 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.
$119 nightly
The price is $134
Oct 19 - Oct 20
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

20. Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.0 out of 10, Wonderful, (6 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
$245 nightly
The price is $277
Nov 2 - Nov 3
Total with taxes and fees
Private Apartment in Southbury 102
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

Best Western Danbury/Bethel

Best Western Danbury/Bethel

10/10 Excellent
"very clean, staff was pleasant and professional"
LAURIE 3-night trip
Posted 2 hours ago
Best Western Danbury/Bethel

Find out more about Sherman

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 $184 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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: Visitors like this Sherman vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Sherman?

With 9 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. While here, Town Meadows and Mildred Strauss and James Morrissey Family Nature Preserves are other places worth a visit.

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.