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Vacation rentals in Sherman

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Top-rated vacation rentals in Sherman

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite

4.91 out of 5 average rating, 294 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Rental unit

4.92 out of 5 average rating, 145 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

Guest suite

4.99 out of 5 average rating, 257 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Guesthouse

4.89 out of 5 average rating, 104 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Guest suite

4.97 out of 5 average rating, 158 reviews

Cozy Scenic New England country retreat w/ hiking

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.

Home

4.88 out of 5 average rating, 182 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Home

5 out of 5 average rating, 212 reviews

Hobbit House of Pawling

Cozy, one of a kind hobbit house with hot tub! **No children under 12 **No pets (Due to allergies) The ultimate private getaway. 2 bedrooms each with king size beds. 2 bathrooms each with walk in shower. Queen size pull out sofa bed in living room. 3 patios, bbq grill, 2 hammocks, 2 fire pits, electric fireplace in living room. -Hike the Appalachian Trail! -Visit all the historic Hudson Valley has to offer! **No parties **No smoking ~Ring Quests upon request at time of booking!

Cabin

4.95 out of 5 average rating, 175 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Cabin

4.95 out of 5 average rating, 138 reviews

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Our Little Creek Cabin is a place to pause. The cabin is located next to a rushing creek, where you can soak in a wood fired hot tub while listening to the sounds of the water. We are minutes from Candlewood Lake & Squantz Pond, where you take take our kayaks out. There are many wineries, breweries, towns to explore, antique shops, ski mountains, and beautiful hiking trails. Here you can simply open the windows to listen to natures sound machine! Find us on IG @thelittlecabins

Home

4.93 out of 5 average rating, 107 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Guesthouse

4.97 out of 5 average rating, 105 reviews

Adorable Cottage in Pastoral Setting

"Farm Cottage" is a charming and comfortable one bedroom cottage apartment that is tucked back in its own private pastoral setting alongside a farm. The cottage is ideally situated between the towns of Kent and New Milford, with easy access to all local attractions. Beautifully furnished with a mixture of antiques and vintage furnishings, the cottage offers a large deck overlooking a rolling meadow plus a full kitchen and washer/dryer. Ideal for one-two guests.

Cabin

4.97 out of 5 average rating, 347 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Vacation rentals for every style

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Hotels

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Unique stays

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Popular amenities for Sherman vacation rentals

Free parking on premises

Air conditioning

Stay near Sherman's top sights

American Pie Company34 locals recommend

White Silo Farm & Winery30 locals recommend

Squantz Pond State Park30 locals recommend

Bulls Covered Bridge27 locals recommend

Sherman Wine & Liquor16 locals recommend

Sherman Players12 locals recommend

Other great vacation rentals in Sherman

Home

4.97 out of 5 average rating, 65 reviews

The Getaway: Beautiful Waterfront - New Milford CT

Cabin

4.94 out of 5 average rating, 67 reviews

Private Hilltop Cabin at Houndcliffe

Chalet

4.89 out of 5 average rating, 27 reviews

jj chalet | Candlewood Lake Vacation Home

Home

4.96 out of 5 average rating, 25 reviews

beautiful country home/ near Mohawk ski area

Cottage

5 out of 5 average rating, 53 reviews

Cheerful one-bedroom cottage with large porch

Home

5 out of 5 average rating, 18 reviews

The Art House: 5-Acre Private Getaway w/ Firepit

Guesthouse

4.99 out of 5 average rating, 95 reviews

Cottage with a Waterfall View

Rental unit

5 out of 5 average rating, 10 reviews

Pawling Village Retreat

Quick stats about vacation rentals in Sherman

Total rentals
40 properties
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Frequently Asked Questions

What are the most popular amenities for House Rentals in Sherman?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Sherman?
Experience the best of Sherman with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Sherman?
Four-legged friends are welcome in Sherman. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Sherman have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Sherman. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Sherman?
Sherman has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Sherman have free parking?
Absolutely! We offer over 20 house rentals with free parking in Sherman. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sherman have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Sherman. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Sherman?
Yes! Work meets play with ease at over 20 vacation rentals in Sherman featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore