Holiday houses in Sherman

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Top-rated holiday rentals in Sherman

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

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Guest favourite

Apartment in Greenwood Lake

4.94 out of 5 average rating, 79 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 115 reviews

Lakefront living/Hot-tub/close to Mt Peter tubing

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront I Family I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Whether you're traveling for the Holidays, visiting family, or looking for a restorative Upstate getaway - this Creekside gem has you covered. - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Guest favourite

Home in Great Barrington

4.95 out of 5 average rating, 20 reviews

Luxury Redo: Hot Tub, Playroom, Sleeps 12

Creamery: Fully Renovated 5 Bedroom Home, sleeps 12 with large screened porch, outdoor patio with seating, sun umbrella, hot tub, fire pit and billiards! Amenities also include: Central AC, all new kitchen appliances, washer/dryer, 4 Smart tvs, fiber internet + good cell service, propane fireplace, blue stone outdoor patio with seating, billiards table, playroom, high quality linens included, Front porch with seating, superior central location: less than 10 to GB, less than 10 to Catamount!

Guest favourite

Home in Woodstock

4.92 out of 5 average rating, 462 reviews

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

Completely Private w/ Exceptional, Expansive Mountain View, All-Seasons Hot Tub and Sauna. Billiards room, Fireplace, Woodstove, Screen Porch, 300 Vinyl records, Full Kitchen, bathtub and Bidet Surrounded by nature, but 2 miles from center of town. Hiking and creek swimming walking distance This property is for Love. La Dolce Vita. The Love of Friends and Family. The Love of Time. Fall in Love here, with the Land and with One-Another. *No checkins are avail Tgiving,Xmas Day, Easter Sunday

Guest favourite

Home in Roxbury

5 out of 5 average rating, 10 reviews

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Superhost

Chalet in Goshen

4.89 out of 5 average rating, 135 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Guest favourite

Townhouse in Hunter

4.92 out of 5 average rating, 72 reviews

Stunning Mountain View Catskill Vacation Escape

Enjoy the BEST LOCATION IN THE CATSKILLS with Scribner's Lodge right next door, Hunter Mountain 1 mile away, Tannersville a town over, Windham mountain 7 miles away, hiking, lakes, restaurants and breweries all around! Amazing 4 bedroom, 3 bathroom townhome with unbeatable views of Hunter Mountain. Stocked with all the essentials, multiple fireplaces, outdoor grill and a new patio! Bring your skis and snowshoes or rent skates for the winter and enjoy the shared outdoor pool in the summer.

Guest favourite

Home in Sheffield

4.9 out of 5 average rating, 115 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favourite

Cabin in Hunter

4.99 out of 5 average rating, 184 reviews

Lakeside log cabin with Mtn views (dog friendly)

Tranquil log cabin on lake 10 min from Windham & Hunter Mtns (dog friendly). If you're searching for a peaceful, dog friendly, Catskill Mtn getaway, then look no more! From the moment you enter this charming waterfront log cabin you'll sense it's Zen vibes. The cabin is tastefully decorated with an open floor plan which includes a wood burning stove, Lg kitchen, Lg bathroom with X-Lg sky lit shower, 1 Lg bedroom with Queen size bed looking onto a covered porch and breathtaking views!

Guest favourite

Home in Putnam Valley

4.96 out of 5 average rating, 55 reviews

Waterfront Lake House

Your ideal fall lakeside retreat! Your ultimate foliage getaway! Immerse yourself in stunning, panoramic views of vibrant foliage from every room. Our lakeside retreat offers cozy, rustic charm, a full equipped kitchen, and direct access to nature. Relax by the fireplace or on the deck as you take in the breathtaking colors of each season. Steps from the lake for kayaking, fishing, or tranquil sunrise views. Book now to experience a unique escape surrounded by nature's beauty!

Guest favourite

Condo in Hunter

4.89 out of 5 average rating, 85 reviews

Cozy Slope Side Retreat

Hunter Mountain Retreat nestled in the Trailside complex is steps from the slopes. During the ski season, you can walk through parking lot & ski down to get your lift ticket. The Kaatskill Mountain Club is on the opposite side of the trails where you can go for dinner or a drink at the bar. Activities include Zipline, Skyride, Disc Golf, Horseback Riding. Trailside is by far the best & most luxurious place to stay in Hunter. Our rates are very reasonable for the luxury & location.

Popular amenities for Sherman holiday rentals

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

Quick stats about holiday rentals in Sherman

  • Total rentals

    50 properties

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 properties include access to Wi-Fi

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Sherman