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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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Sherman vacation rentals

Desk, WiFi, bed sheets

1. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
$260 nightly
The price is $294
Sep 9 - Sep 10
Total with taxes and fees
Private Apartment in Southbury 105
Private kitchen

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
$128 nightly
The price is $144
Sep 1 - Sep 2
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
Property grounds

3. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
$183 nightly
The price is $207
Sep 7 - Sep 8
Total with taxes and fees
Hoppy Hill Farm House
1 bedroom, internet, bed sheets

4. 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
Aug 24 - Aug 25
Total with taxes and fees
Welcome to Sweet Abby Rose!
Smart TV, fireplace, books

5. 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, (23 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
$189 nightly
The price is $214
Aug 23 - Aug 24
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Cookware/dishes/utensils

6. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
$634 nightly
The price is $717
Aug 24 - Aug 25
Total with taxes and fees
Awesome Lake Home with tons of fun!
Outdoor dining

7. 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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
$207 nightly
The price is $234
Aug 25 - Aug 26
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Property grounds

8. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (9 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
$118 nightly
The price is $134
Aug 31 - Sep 1
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Exterior

9. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (36 reviews)
"Everything was perfect and it's a great place to stay. Highly recommended and the folks there are A+."
United States
Bob
$113 nightly
The price is $127
Sep 14 - Sep 15
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Coffee/tea maker, fridge, microwave, oven

10. "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.
$515 nightly
The price is $582
Sep 14 - Sep 15
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace

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
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
$415 nightly
The price is $450
Aug 24 - Aug 25
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Coffee/tea maker, fridge, microwave, oven

12. Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
10.0 out of 10, Exceptional, (1 review)
"Pro Unit very clean, check in was easy and host was responsive to issues 24/7.Unit is large with new appliances in full kitchen.It is located in a beautiful rural area of CT. I highly recommend it"
United States
Daniel R.
$194 nightly
The price is $220
Aug 20 - Aug 21
Total with taxes and fees
Private Apartment in Southbury 104
Exterior

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
$178 nightly
The price is $201
Aug 20 - Aug 21
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Coffee/tea maker, fridge, microwave, oven

14. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (4 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
$237 nightly
The price is $267
Aug 23 - Aug 24
Total with taxes and fees
Private Apartment in Southbury 103
Interior

15. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
$184 nightly
The price is $199
Sep 14 - Sep 15
Total with taxes and fees
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Property grounds

16. Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
10.0 out of 10, Exceptional, (1 review)
$495 nightly
The price is $560
Aug 24 - Aug 25
Total with taxes and fees
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Interior

17. 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, (14 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
$246 nightly
The price is $278
Aug 20 - Aug 21
Total with taxes and fees
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Outdoor dining

18. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (58 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
$1,719 nightly
The price is $1,947
Sep 17 - Sep 18
Total with taxes and fees
Candlewood Lake Retreat with Private Dock
Interior

19. 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.
$244 nightly
The price is $276
Sep 9 - Sep 10
Total with taxes and fees
Private Apartment in Southbury 101
Outdoor dining

20. Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (5 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$118 nightly
The price is $134
Aug 31 - Sep 1
Total with taxes and fees
Glamping, family fun, pet friendly
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

Ethan Allen Hotel

Ethan Allen Hotel

10/10 Excellent
"It's a wonderful property, just a bit dated."
Michael 1-night trip
Posted 12 hours ago
Ethan Allen Hotel

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 $134 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.