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

Sherman Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Sherman holiday rentals

A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

1. 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$174
includes taxes & fees
9 Sept - 10 Sept
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A view through a window with a clear sky and lush greenery outside.

2. 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.
The price is AU$420
includes taxes & fees
22 Sept - 23 Sept
Private Apartment in Southbury 101
A modern kitchen with white cabinets, stainless steel appliances, and a grey wooden floor.

3. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is AU$390
includes taxes & fees
6 Sept - 7 Sept
Private Apartment in Southbury 103
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

4. 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.
The price is AU$367
includes taxes & fees
10 Sept - 11 Sept
Private Apartment in Southbury 104
A bedroom with a bed, bedside tables, a lamp, and a door leading to a laundry area.

5. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is AU$348
includes taxes & fees
3 Sept - 4 Sept
Private Apartment in Southbury 105
A white house with a wooden staircase leading to a porch.

6. 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
The price is AU$172
includes taxes & fees
10 Sept - 11 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
A modern kitchen with white cabinets, a black countertop, and a dining area with a table and chairs.

7. 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.
The price is AU$353
includes taxes & fees
10 Sept - 11 Sept
Private Apartment in Southbury 102
A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

8. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
The price is AU$539
includes taxes & fees
8 Sept - 9 Sept
The Jefferson Guest House, Spacious, Special Views
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

9. 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, (16 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is AU$385
includes taxes & fees
3 Sept - 4 Sept
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is AU$327
includes taxes & fees
7 Sept - 8 Sept
The Perch in the Purchase -- Cozy, unique, and private
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

11. Renovated Retreat with Heated Pool

Renovated Retreat with Heated Pool
Redding
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house, very clean, spacious and a great host!!!"
United States
Alejandro A.
The price is AU$1,148
includes taxes & fees
27 Sept - 28 Sept
Renovated Retreat with Heated Pool
A hot tub in a backyard with a house, trees, and a clear sky.

12. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is AU$4,892
includes taxes & fees
1 Oct - 2 Oct
Las Flores Villa
A two-story house with a deck, outdoor seating, and string lights.

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

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
9.0 out of 10, Wonderful, (2 reviews)
"Very nice hosts and immaculately clean property. Hot tub was great. My only mention is that there isn’t actually any lake access which was misleading. We did use the hosts’ kayaks and put them on our cars to go boating which was free, but swimming is not free and about a 10 min drive away. The hosts also live above the suite (not mentioned) but we had a private entrance."
United States
Kaitlyn C.
The price is AU$769
includes taxes & fees
10 Sept - 11 Sept
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
A multi-story house with a dock and boats, surrounded by dense forest.

14. North Cliff House - Private Dock & Sauna

North Cliff House - Private Dock & Sauna
Danbury
10.0 out of 10, Exceptional, (8 reviews)
"Great house and views of the lake. Very modern and comfortable with everything you need. "
United States
Ronald L.
The price is AU$1,614
includes taxes & fees
7 Sept - 8 Sept
North Cliff House - Private Dock & Sauna
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

15. 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, (1 review)
"Clean and close to activitys"
United States
randall
The price is AU$204
includes taxes & fees
7 Sept - 8 Sept
Cozy private room in a shared home with a Full-size bed and private bathroom.
A patio with a round table and chairs, overlooking a body of water and a forested area during sunset.

16. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (59 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is AU$2,390
includes taxes & fees
17 Sept - 18 Sept
Candlewood Lake Retreat with Private Dock
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

17. 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.
The price is AU$260
includes taxes & fees
3 Sept - 4 Sept
Welcome to Sweet Abby Rose!
A living room with a fireplace, two armchairs, a sofa, and a TV.

18. 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)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is AU$301
includes taxes & fees
3 Sept - 4 Sept
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

19. 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.
The price is AU$287
includes taxes & fees
15 Sept - 16 Sept
Hoppy Hill Farm House
Two camping tents set up in a forest with chairs and a wooden platform nearby.

20. 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, (11 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.
The price is AU$226
includes taxes & fees
7 Sept - 8 Sept
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sherman Hotel Reviews

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent
"Buena atención en general"
Luis Alberto 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Danbury-Bethel

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$204 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.