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

Our top choices for Sherman vacation rentals

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

1. 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 ￥169,476
￥289,670 total
includes taxes & fees
Sep 17 - Sep 18
Candlewood Lake Retreat with Private Dock
A white house with a wooden staircase leading to a porch.

2. 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 ￥13,782
￥18,975 total
includes taxes & fees
Sep 9 - Sep 10
Cozy One Bedroom Apartment Centrally Located in Southbury
A room with a Yale banner, a white robe hanging on a rack, and a light switch on the wall.

3. 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
The price is ￥63,285
￥112,546 total
includes taxes & fees
Sep 9 - Sep 10
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern living room with a flat-screen TV mounted on a white wall, a clock, and a minimalist design.

4. 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 ￥13,907
￥19,118 total
includes taxes & fees
Sep 8 - Sep 9
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
A two-story house with a deck, outdoor seating, and string lights.

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

Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
Danbury
9.6 out of 10, Exceptional, (4 reviews)
"Paula was an amazing host that helped us with our luggage as soon as we arrived in the wee hours of the night. The amount of love she has for her property shows, as everything you could need and more is there. A lovely stay, thank you so much!"
United States
Angelina L.
The price is ￥52,035
￥86,873 total
includes taxes & fees
Sep 7 - Sep 8
Brand New Lakeview Suite: Hot Tub, Pet friendly & 4 Parking Spots
A covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

6. 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 ￥17,189
￥32,173 total
includes taxes & fees
Sep 7 - Sep 8
Hoppy Hill Farm House
A living room with a fireplace, two armchairs, a sofa, and a TV.

7. 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 ￥25,900
￥33,379 total
includes taxes & fees
Sep 7 - Sep 8
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

8. 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 ￥10,626
￥22,533 total
includes taxes & fees
Sep 7 - Sep 8
Cozy private room in a shared home with a Full-size bed and private bathroom.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

9. "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 ￥31,643
￥90,244 total
includes taxes & fees
Sep 15 - Sep 16
"Country outside the city " 3 bedrooms 2 full bathrooms
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 ￥22,783
￥36,084 total
includes taxes & fees
Sep 7 - Sep 8
The Perch in the Purchase -- Cozy, unique, and private
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

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, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥39,065
￥70,619 total
includes taxes & fees
Sep 21 - Sep 22
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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!

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 ￥15,626
￥28,958 total
includes taxes & fees
Sep 7 - Sep 8
Welcome to Sweet Abby Rose!
A modern kitchen with white cabinets, stainless steel appliances, and a grey wooden floor.

13. 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 ￥17,814
￥39,823 total
includes taxes & fees
Sep 9 - Sep 10
Private Apartment in Southbury 103
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

14. 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 ￥77,349
￥109,768 total
includes taxes & fees
Sep 8 - Sep 9
Chestnut on Willow Lake
A hot tub in a backyard with a house, trees, and a clear sky.

15. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is ￥421,902
￥547,691 total
includes taxes & fees
Oct 1 - Oct 2
Las Flores Villa
A modern kitchen with white cabinets, a dining area with a black table and chairs, and a large window with curtains.

16. Private Apartment in Southbury 105

Private Apartment in Southbury 105
Southbury
The price is ￥18,126
￥40,495 total
includes taxes & fees
Sep 8 - Sep 9
Private Apartment in Southbury 105
A spacious living room with a foosball table, a large flat-screen TV, and a fireplace.

17. 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 ￥93,600
￥164,265 total
includes taxes & fees
Sep 8 - Sep 9
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
A modern kitchen with white cabinets, stainless steel appliances, and a dining table with chairs.

18. 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 ￥13,501
￥34,238 total
includes taxes & fees
Sep 7 - Sep 8
Private Apartment in Southbury 104
A room with a bed, a couch, a desk with a computer, and various wall decorations.

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

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is ￥34,533
￥46,062 total
includes taxes & fees
Oct 5 - Oct 6
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A glass-top table with a woven placemat, a vase with white flowers, and a view of a balcony through a door with curtains.

20. 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 ￥33,596
￥42,854 total
includes taxes & fees
Sep 7 - Sep 8
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
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

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Room, bedding and bathroom were very clean."
Shari 1-night trip
Posted 3 hours ago
Wyndham Southbury

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 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.