Sherman Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Sherman holiday rentals

A kitchen with a central island, bar stools, a dining table with chairs, pendant lights, and a refrigerator.

1. Awesome Lake Home with tons of fun!

New Fairfield

W Y.

HK$6,084 total

includes taxes & fees

20 Sept - 21 Sept

A patio with a round table and chairs, overlooking a body of water and a forested area during sunset.

2. Candlewood Lake Retreat with Private Dock

New Milford

Jenny B.

HK$15,069 total

includes taxes & fees

17 Sept - 18 Sept

A living room with a fireplace, two armchairs, a sofa, and a TV.

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

Kent

Joy P.

HK$1,683 total

includes taxes & fees

25 Aug - 26 Aug

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

Brookfield

HK$7,503 total

includes taxes & fees

8 Sept - 9 Sept

A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

5. Hoppy Hill Farm House

Dover Plains

Chuck S.

HK$1,623 total

includes taxes & fees

7 Sept - 8 Sept

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

Holmes

pamela w.

HK$4,679 total

includes taxes & fees

2 Sept - 3 Sept

A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

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

Carmel Hamlet

Robert T.

HK$3,688 total

includes taxes & fees

22 Sept - 23 Sept

A two-story house with a deck, outdoor seating, and string lights.

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

Danbury

HK$4,560 total

includes taxes & fees

1 Sept - 2 Sept

A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

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

Southbury

Chris

HK$1,834 total

includes taxes & fees

25 Aug - 26 Aug

A spacious living room with a foosball table, a large flat-screen TV, and a fireplace.

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

Carmel Hamlet

Jasmine G.

HK$8,233 total

includes taxes & fees

25 Aug - 26 Aug

An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

11. Rustic Cabin in Fishkill!

Fishkill

Nadja E.

HK$3,607 total

includes taxes & fees

25 Aug - 26 Aug

A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

12. Welcome to Sweet Abby Rose!

Brewster

Yasmin G.

HK$1,461 total

includes taxes & fees

25 Aug - 26 Aug

Two camping tents set up in a forest with chairs and a wooden platform nearby.

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

Dover Plains

JoAnna S.

HK$1,048 total

includes taxes & fees

31 Aug - 1 Sept

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.

Morris

Joe K.

HK$2,181 total

includes taxes & fees

26 Aug - 27 Aug

A kitchen with a marble island, wooden cabinets, a clock, and a window with a view of trees.

15. The Jefferson Guest House, Spacious, Special Views

Litchfield

"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!"

genevieve

HK$3,119 total

includes taxes & fees

25 Aug - 26 Aug

A white house with a steeply pitched roof and a small tower-like structure.

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

Millbrook

Lindsay S.

HK$3,902 total

includes taxes & fees

25 Aug - 26 Aug

A white house with a wooden staircase leading to a porch.

17. Cozy One Bedroom Apartment Centrally Located in Southbury

Southbury

Bob

HK$993 total

includes taxes & fees

22 Sept - 23 Sept

A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

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

Millbrook

Beth E.

HK$6,590 total

includes taxes & fees

31 Aug - 1 Sept

A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

19. Chestnut on Willow Lake

Fishkill

Doria W.

HK$5,580 total

includes taxes & fees

26 Aug - 27 Aug

A modern kitchen with a central island, pendant lights, and a view of the outdoors.

20. Renovated Retreat with Heated Pool

Redding

Alejandro A.

HK$7,405 total

includes taxes & fees

14 Sept - 15 Sept

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Top Sherman Hotel Reviews

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

10/10 Excellent

"Clean room. Friendly staff."

Ethan Allen Hotel

8/10 Good

"An easy overnight stay for our family of 5. Loved that all the furniture was Ethan Allen - felt so much better than typical hotel furniture. Loved the complimentary cookies water and coffee. Only minor complaints were we had to wait an unusual length of time to check in with only 1 group ahead of us, and we were only provided with 2 towels in a room for 5. If we were staying longer I would have asked for more."

Best Western Danbury/Bethel

8/10 Good

"The room could absolutely use a clean, curtains and bedspread had some stain/spots on them. Super easy to park here, breakfast was nice, daughter enjoyed make your own waffle iron. Not super gluten free friendly, they had a yogurt machine. Property is possibly in the process of removing all carpet, the room had none but the hallway had pieces taped down. Otherwise room felt good, air conditioner worked and easy to get to hotel."

Best Western Plus The Inn & Suites At The Falls

10/10 Excellent

"Loved loved loved the room on the 2nd floor! High ceilings ! Pretty drapes! Gorgeous round window along a huge rectangular window looking out on the water! Very spacious! Pretty lighting! Great breakfast! Comfy beds ! Loved staying here! Staff was so thoughtful and nice! Thank you"

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent

"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared to be a utility room that was active early in the morning. I could hear footsteps throughout the day. The dinner was overrated, but the breakfast and lunch were delicious."

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:

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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.

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Check prices for these dates

Our top choices for Sherman holiday rentals

1. Awesome Lake Home with tons of fun!

2. Candlewood Lake Retreat with Private Dock

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

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

5. Hoppy Hill Farm House

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

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

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

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

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

11. Rustic Cabin in Fishkill!

12. Welcome to Sweet Abby Rose!

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

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

15. The Jefferson Guest House, Spacious, Special Views

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

17. Cozy One Bedroom Apartment Centrally Located in Southbury

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

19. Chestnut on Willow Lake

20. Renovated Retreat with Heated Pool

Find holiday rentals that suit your style

Top Sherman Hotel Reviews

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

Ethan Allen Hotel

Hilton Garden Inn Danbury

Best Western Danbury/Bethel

Best Western Plus The Inn & Suites At The Falls

Mayflower Inn & Spa, Auberge Collection

Days Inn by Wyndham Ridgefield

Find out more about Sherman

Frequently asked questions

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