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Sherman Holiday Rentals

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Holiday Rentals in Sherman

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (28)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.0 out of 10, Wonderful, (21)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Lake Oasis with Firepit, Game room and Kayaks

8.8 out of 10, Excellent, (3)
"Our weekend at Rory’s home was everything and then some. The hospitality was truly unmatched. Rory bought us a new grill, provided pizza, and gave us fantastic suggestions to go do in the area. There was so much to do around the house between using the kayaks during the day and ending the night by the bonfire. I highly recommend staying here for a weekend getaway, reunion, or even to just unwind and get away from the city. 10/10 experience, would absolutely stay here again! "
Lake Oasis with Firepit, Game room and Kayaks

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is NZ$719
includes taxes & fees
28 Aug - 29 Aug
Rustic Cabin in Fishkill!

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.0 out of 10, Wonderful, (10)
"The house was everything that it is advertised to be. When we arrived, we found it very clean and spacious enough for five adults and two dogs. The hosts were considerate and extremely gracious. The farm is picturesque, chickens and goats look very well cared for and added to the charm. …no worries if you are not an animal lover, the goats and chickens stay far enough away that you can simply not take any notice of them. The beautiful village of Millbrook is just 4 minutes down the road...
Pet-friendly Cottage at Historic Millbrook Farm Estate

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (44)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford

10.0 out of 10, Exceptional, (4)
"This ground level apartment is comfortable and exceptionally clean, and above all its location in a bucolic setting made our two night stay peaceful and restful. Knowing location of the key made the check-in very easy, and the kitchen facilities met our needs. "
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (80)
"Great place! Loved waking up to a water view. Very peaceful."
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

10.0 out of 10, Exceptional, (11)
"The house worked very well for our family holiday. Very clean, had everything we needed "
The price is NZ$1,159
includes taxes & fees
1 Sept - 2 Sept
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (191)
"We loved the house, it was very quiet, the view of the lake was beautiful (even though it was rainy and cloudy). The decoration was really nice and it felt super cozy. The host was also very responsive. "
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (48)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (46)
"Wonderful! Elizabeth and John made everything seamless and enjoyable. Terrific location! "
Waterfront Family Retreat on Candlewood Lake

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (26)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is NZ$1,053
includes taxes & fees
28 Aug - 29 Aug
Hickory on Willow Lake

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

10.0 out of 10, Exceptional, (15)
"We had a great stay and had everything we needed!"
The price is NZ$1,478
includes taxes & fees
1 Sept - 2 Sept
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

The Hideaway

10.0 out of 10, Exceptional, (4)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
The price is NZ$505
includes taxes & fees
27 Sept - 28 Sept
The Hideaway
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

Find out more about Sherman

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 favorite 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 depends 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 NZ$505 per night. Entering your travel dates in the search wizard you might find 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, King Bed, 1 Hour & 15 Min from NYC etc!: This holiday home rental outside of Sherman is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

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.