Book Holiday Homes in Sherman

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Featured Holiday Homes in Sherman

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

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

Carmel Hamlet NY
Stay at this holiday home in Carmel. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in their reviews. Popular attractions ...
Opens in a new windowPrivacy in the hills one hour from NYC and minutes to Breakneck Mtn.
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction NY
Stay at this holiday home in Hopewell Junction. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Canopus Beach and Clarence Fahnestock State ...
Opens in a new window1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

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

Danbury CT
Stay at this holiday home in Danbury. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bear Mountain Reservation and Candlewood Plaza Shopping ...
Opens in a new windowBeautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount
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Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam

Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam

New Fairfield CT
Stay at this family-friendly holiday home in New Fairfield. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Squantz Pond State Park and ...
Opens in a new windowEscape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Bethlehem CT
Stay at this holiday home in Bethlehem. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Abbey of Regina Laudis and Flanders Nature Center ...
Opens in a new windowNature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

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

New Fairfield CT
Stay at this holiday home in New Fairfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Squantz Pond State Park and Candlewood Lake ...
Opens in a new windowLakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Historic Hideaway with Lake Access!

Historic Hideaway with Lake Access!

South Salem NY
Stay at this holiday home in South Salem. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mamanasco Beach and Aldrich Contemporary Art ...
Opens in a new windowHistoric Hideaway with Lake Access!
Mountain View Getaway

Mountain View Getaway

West Cornwall CT
Stay at this ski holiday home in Cornwall. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Music Mountain and West Cornwall Covered Bridge ...
Opens in a new windowMountain View Getaway
Bluebird Valley Farmhouse

Bluebird Valley Farmhouse

Millerton NY
Stay at this holiday home in Millerton. Enjoy a garden, laundry facilities and patios. Popular attractions Harlem Valley Rail Trail and Veterans Field are located ...
Opens in a new windowBluebird Valley Farmhouse
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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.

Sherman Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Sherman vacation homes are the perfect way for you to wing it.

Holiday houses in Sherman let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Sherman in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Sherman adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Sherman with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Sherman vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Sherman Holiday Homes essential information

Accommodation
251 Holiday Homes
Lowest Price
NZ$179
Highest Price
NZ$347
Popular accommodation
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn. , 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views, Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount, Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam, Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook, Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed, Historic Hideaway with Lake Access!, Mountain View Getaway, Bluebird Valley Farmhouse

Top trending hotels in Sherman

Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is NZ$186 per night from 17 May to 18 May
NZ$186
17 May - 18 May
includes taxes & fees
Stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowBest Western Danbury/Bethel
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is NZ$179 per night from 17 May to 18 May
NZ$179
17 May - 18 May
includes taxes & fees
Stay at this business-friendly hotel in Southbury. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowWyndham Southbury
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
The price is NZ$347 per night from 10 May to 11 May
NZ$347
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Danbury. Enjoy free Wi-Fi, free parking and room service. Our guests praise the restaurant and the helpful staff in their ...
Opens in a new windowHotel Zero Degrees Danbury
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Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 10 May to 11 May
NZ$225
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Danbury. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowEthan Allen Hotel
Don't see what you're looking for?
See all available properties in Sherman
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.