Vacation rentals in Sherman

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Top-rated vacation rentals in Sherman

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Guest favorite

Apartment in Kent

4.93 out of 5 average rating, 127 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.*

Dec 6 – 13

R2,980 ZAR per night

Guest favorite

Home in Danbury

4.99 out of 5 average rating, 336 reviews

BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!

Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants

Sep 4 – 11

R3,025 ZAR per night

Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 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.

Sep 6 – 13

R3,164 ZAR per night

Guest favorite

Guest suite in Sherman

4.98 out of 5 average rating, 134 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.

Apr 21 – 26

R2,772 ZAR per night

Superhost

Home in New Milford

4.88 out of 5 average rating, 165 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.

Jan 24 – 31

R4,452 ZAR per night

Guest favorite

Cabin in New Milford

4.95 out of 5 average rating, 146 reviews

The Cottage on Babbling Brook

Cozy, rustic cottage. Beautifully overlooking Wimsink Brook, with 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.

Nov 29 – Dec 6

R4,544 ZAR per night

Guest favorite

Guest suite in Dover Plains

4.91 out of 5 average rating, 262 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. Thunder Ridge ski mountain and Daryl Hall’s bar only 15 mins away. Take a ride to near-by towns (Kent, Millbrook, Amenia, Wassaic) for great food, coffee shops, antiques, parks, breweries and vineries.

Jul 9 – 16

R2,846 ZAR per night

Guest favorite

Home in Pawling

4.9 out of 5 average rating, 273 reviews

Appalachian Trail House! Easy access to NYC trains

Hike the Appalachian Trail! This is a cozy 3 bedroom, 1 bath, full basement and 3 acres of land. Located in town of Pawling, NY, about 90 minutes from NYC. Walking distance from Appalachian Trail train stop. Enjoy mother nature at it's finest with a short hike up historic Quaker Hill section of the Appalachian Trail. We accept up to 2 well behaved pets under 40 lbs. There is a $50 fee per pet. For companion and service dogs/pets, paperwork must be submitted before stay.

Nov 27 – Dec 4

R3,806 ZAR per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Jan 23 – 30

R2,281 ZAR per night

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 308 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.

Oct 31 – Nov 7

R8,775 ZAR per night

Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 256 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars. Find us on IG @thelittlecabins

Sep 29 – Oct 6

R7,694 ZAR per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Mar 13 – 20

R1,796 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Sherman vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Sherman's top sights

American Pie Company34 locals recommend

The Old Oak Tavern7 locals recommend

White Silo Farm & Winery30 locals recommend

Salinas Restaurant and Pizza3 locals recommend

The Painted Lemon8 locals recommend

Sacred Grounds Coffee Roasters4 locals recommend

Other great vacation rentals in Sherman

Guest favorite

Guest suite in Kent

5.0 out of 5 average rating, 56 reviews

Bright 1-bedroom in walking distance to town

Mar 19 – 26

R2,385 ZAR per night

Guest favorite

Guesthouse in New Milford

5.0 out of 5 average rating, 43 reviews

Luxury in the Litchfield Hills

Jan 9 – 16

R4,025 ZAR per night

Guest favorite

Home in Kent

4.9 out of 5 average rating, 10 reviews

Perfection in Litchfield County, 5 BR with Pool

Dec 12 – 19

R10,152 ZAR per night

Guest favorite

Guesthouse in Sharon

5.0 out of 5 average rating, 64 reviews

Cottage with a Waterfall View

Sep 26 – Oct 3

R2,086 ZAR per night

Guest favorite

Apartment in Pawling

5.0 out of 5 average rating, 15 reviews

Quiet Studio Apartment in Pawling

Nov 8 – 15

R3,270 ZAR per night

Guest favorite

Cottage in Pawling

5.0 out of 5 average rating, 61 reviews

Twin Lakes Designer A-frame Stone Cottage

Dec 9 – 16

R6,929 ZAR per night

Guest favorite

Cabin in New Milford

5.0 out of 5 average rating, 48 reviews

Stylish Cabin Escape with Chef's Kitchen & Firepit

Nov 7 – 14

R8,927 ZAR per night

Guest favorite

Chalet in New Milford

4.89 out of 5 average rating, 9 reviews

jj chalet | A Modern Lake House Retreat

Aug 27 – Sep 3

R6,734 ZAR per night

Show all

Quick stats about vacation rentals in Sherman

Total rentals
50 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.8K reviews

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 free parking, over 20 homes with wifi, 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 $60 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 30 vacation rentals in Sherman featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Sherman

Top-rated vacation rentals in Sherman

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Sherman vacation rentals

Stay near Sherman's top sights

Other great vacation rentals in Sherman

Guest suite in Kent

Guesthouse in New Milford

Home in Kent

Guesthouse in Sharon

Apartment in Pawling

Cottage in Pawling

Cabin in New Milford

Chalet in New Milford

Quick stats about vacation rentals in Sherman

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What are the most popular amenities for House Rentals in Sherman?

How much does it cost to stay in house rentals in Sherman?

Are there pet-friendly vacation rentals in Sherman?

Do house rentals in Sherman have air conditioning?

Are there family-friendly vacation rentals in Sherman?

Do house rentals in Sherman have free parking?

Do house rentals in Sherman have a kitchen?

Are there vacation rentals with a dedicated workspace in Sherman?

Destinations to explore