Holiday houses in Sherman

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Top-rated holiday rentals in Sherman

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Guest favourite

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.*

16 – 23 Oct

$1,913 AUD total

Guest favourite

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

2 – 9 Jan

$1,917 AUD total

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

2 – 9 Aug

$972 AUD total

Guest favourite

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.

19 – 26 Apr

$1,995 AUD total

Superhost

Home in New Milford

4.88 out of 5 average rating, 163 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.

6 – 13 Oct

$3,207 AUD total

Guest favourite

Cabin in New Milford

4.95 out of 5 average rating, 145 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.

1 – 8 May

$2,579 AUD total

Guest favourite

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.

18 – 25 Aug

$1,815 AUD total

Guest favourite

Home in Pawling

4.9 out of 5 average rating, 272 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.

18 – 25 Jan

$2,426 AUD total

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 183 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.

12 – 19 Mar

$1,543 AUD total

Guest favourite

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.

20 – 27 Oct

$5,877 AUD total

Guest favourite

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

18 – 25 Feb

$3,935 AUD total

Guest favourite

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.

24 – 31 Mar

$1,201 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Sherman holiday rentals

Kitchen

Wi-Fi

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 holiday rentals in Sherman

Guest favourite

Guest suite in Kent

5.0 out of 5 average rating, 55 reviews

Bright 1-bedroom in walking distance to town

20 – 27 Feb

$1,565 AUD total

Guest favourite

Guesthouse in New Milford

5.0 out of 5 average rating, 43 reviews

Luxury in the Litchfield Hills

11 – 18 May

$2,582 AUD total

Guest favourite

Home in Kent

4.9 out of 5 average rating, 10 reviews

Perfection in Litchfield County, 5 BR with Pool

24 Feb – 3 Mar

$7,318 AUD total

Guest favourite

Apartment in Amenia

5.0 out of 5 average rating, 22 reviews

Amenia Main St Cozy Studio

11 – 18 Sept

$921 AUD total

Guest favourite

Home in Pawling

4.96 out of 5 average rating, 23 reviews

Country Village Getaway

22 – 29 Oct

$1,949 AUD total

Guest favourite

Home in New Fairfield

4.96 out of 5 average rating, 56 reviews

Hilltop Retreat- Lakefront with Dock

30 Sept – 7 Oct

$4,227 AUD total

Guest favourite

Cabin in New Milford

5.0 out of 5 average rating, 48 reviews

Stylish Cabin Escape with Chef's Kitchen & Firepit

7 – 14 Dec

$6,007 AUD total

Guest favourite

Guesthouse in Sharon

5.0 out of 5 average rating, 63 reviews

Cottage with a Waterfall View

26 Sept – 3 Oct

$1,453 AUD total

Show all

Quick stats about holiday rentals in Sherman

Total rentals	50 properties
Wi-Fi availability	50 properties include access to Wi-Fi
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

Holiday houses in Sherman

Top-rated holiday rentals in Sherman

Apartment in Kent

Home in Danbury

Guest suite in Watertown

Guest suite in Sherman

Home in New Milford

Cabin in New Milford

Guest suite in Dover Plains

Home in Pawling

Apartment in Brookfield

Cabin in Sherman

Cabin in New Fairfield

Guest suite in Morris

Holiday rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Sherman holiday rentals

Stay near Sherman's top sights

Other great holiday rentals in Sherman

Guest suite in Kent

Guesthouse in New Milford

Home in Kent

Apartment in Amenia

Home in Pawling

Home in New Fairfield

Cabin in New Milford

Guesthouse in Sharon

Quick stats about holiday rentals in Sherman

Total rentals

Wi-Fi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore