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

Our top choices for Sherman holiday rentals

Cookware/dishes/utensils

1. 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.
The price is HK$3,528
HK$6,084 total
includes taxes & fees
20 Sept - 21 Sept
Awesome Lake Home with tons of fun!
Outdoor dining

2. 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.
The price is HK$8,914
HK$15,069 total
includes taxes & fees
17 Sept - 18 Sept
Candlewood Lake Retreat with Private Dock
Smart TV, fireplace, books

3. 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.
The price is HK$1,299
HK$1,683 total
includes taxes & fees
25 Aug - 26 Aug
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Private kitchen

4. Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families

Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families
Brookfield
The price is HK$4,234
HK$7,503 total
includes taxes & fees
8 Sept - 9 Sept
Gorgeous 4-bedroom house on lovely Candlewood Lake perfect for families
Property grounds

5. 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 HK$862
HK$1,623 total
includes taxes & fees
7 Sept - 8 Sept
Hoppy Hill Farm House
Coffee/tea maker, fridge, microwave, oven

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 HK$1,644
HK$4,663 total
includes taxes & fees
1 Sept - 2 Sept
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace

7. 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.
The price is HK$2,038
HK$3,688 total
includes taxes & fees
22 Sept - 23 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Property grounds

8. 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)
The price is HK$2,745
HK$4,560 total
includes taxes & fees
1 Sept - 2 Sept
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Outdoor dining

9. 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 HK$1,143
HK$1,834 total
includes taxes & fees
25 Aug - 26 Aug
The Perch in the Purchase -- Cozy, unique, and private
Smart TV, fireplace, video games, DVD player

10. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is HK$4,696
HK$8,233 total
includes taxes & fees
25 Aug - 26 Aug
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Exterior

11. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,372
HK$3,607 total
includes taxes & fees
25 Aug - 26 Aug
Rustic Cabin in Fishkill!
1 bedroom, Internet, bed sheets

12. 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 HK$784
HK$1,461 total
includes taxes & fees
25 Aug - 26 Aug
Welcome to Sweet Abby Rose!
Property grounds

13. 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, (10 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 HK$628
HK$1,048 total
includes taxes & fees
31 Aug - 1 Sept
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Interior

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, (14 reviews)
"Very clean & cozy with everything we needed!"
United States
Joe K.
The price is HK$1,686
HK$2,181 total
includes taxes & fees
26 Aug - 27 Aug
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Coffee/tea maker, fridge, microwave, oven

15. 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 HK$2,413
HK$3,119 total
includes taxes & fees
25 Aug - 26 Aug
The Jefferson Guest House, Spacious, Special Views
Exterior

16. 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
9.6 out of 10, Exceptional, (5 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is HK$2,509
HK$3,902 total
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior

17. 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 HK$727
HK$993 total
includes taxes & fees
22 Sept - 23 Sept
Cozy One Bedroom Apartment Centrally Located in Southbury
Interior

18. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is HK$3,136
HK$6,590 total
includes taxes & fees
30 Aug - 31 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Exterior

19. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is HK$3,881
HK$5,580 total
includes taxes & fees
25 Aug - 26 Aug
Chestnut on Willow Lake
Coffee/tea maker, fridge, microwave, oven

20. 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 HK$3,724
HK$7,405 total
includes taxes & fees
14 Sept - 15 Sept
Renovated Retreat with Heated Pool
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

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

10/10 Excellent
"Clean room. Friendly staff."
Adelia 2-night trip
Posted 5 hours ago
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Find out more about Sherman

Search for holiday rentals in Sherman on Expedia! You can easily find your home rentals, villas, holiday apartments in Sherman using one of the methods below:

  • View our selection of featured holiday rentals in Sherman
  • Use the map to find apartments and other holiday homes in the Sherman neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sherman while they last

Look no further and take a look at our great range of rental properties in Sherman!

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.