Holiday rentals in Sharon

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Top-rated holiday rentals in Sharon

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Guest favourite

Flat in Amenia

4.92 out of 5 average rating, 105 reviews

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Guest favourite

Home in Amenia

4.97 out of 5 average rating, 123 reviews

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

Top guest favourite

Guest house in Millerton

4.98 out of 5 average rating, 104 reviews

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY & Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking & skiing. Easy walk to antique shops & delicious restaurants or put your feet up and relax! 1.5 baths, living room with flat screen TV, dining room & fully equipped kitchen & expansive deck to take in the view. Rent with House in The Pines for a larger group

Top guest favourite

Holiday home in Warren

4.98 out of 5 average rating, 166 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Superhost

Guest house in Dover Plains

4.87 out of 5 average rating, 115 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 favourite

Cottage in West Cornwall

4.93 out of 5 average rating, 154 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Guest favourite

Home in West Cornwall

4.91 out of 5 average rating, 188 reviews

Charming CT Country Farmhouse for group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining.

Top guest favourite

Home in Cornwall

4.99 out of 5 average rating, 103 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Guest favourite

Cabin in Pine Plains

4.97 out of 5 average rating, 233 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

Superhost

Flat in Millerton

4.79 out of 5 average rating, 107 reviews

The Studio

Millerton, NY is a weekenders dream! Enjoy a peaceful stay at our newly renovated Studio fully furnished and with a Queen Bed. You’re just a short walk from everything the village of Millerton has to offer! Grab a bite to eat at the popular Oakhurst Diner or indulge in a coffee at Irving Farm Coffee Roasters. After that, make your way to Westerlind to do a little shopping, pop into Oblong Books or enjoy the charm of an old time film theater by checking out The Movie house.

Guest favourite

Guest suite in Millerton

4.93 out of 5 average rating, 366 reviews

Sunset 60 mile view

ROMANTIC LUXURY! Spring has SPRUNG! Gorgeous warm weather; fresh, crisp mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, charcoal bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV.

Guest favourite

Cottage in North East

4.86 out of 5 average rating, 155 reviews

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. An idyllic setting in which to unplug and enjoy nature. Walk to the 42-mile Rail Trail, strap your bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventure!

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Other great holiday rentals in Sharon

Guest suite in Warren

4.78 out of 5 average rating, 223 reviews

Rustic Farmhouse Suite; Cozy; Litchfield County

ShaneRating, 5 stars5 days ago

Peter was a friendly, helpful, welcoming host. The Suite at his place had everything we needed and was a cozy, quiet retreat for us and the perfect getaway. We enjoyed our stay and would definitely stay again and recommend it to friends!

Guest favourite

Home in Cornwall

4.88 out of 5 average rating, 17 reviews

Gunn Brook Mountain House

KathrynRating, 5 stars1 week ago

This charming, rural home has a touch of mid-century fun throughout. But the best part is the gorgeous lawn and waking up to the sound of the rushing brook right outside the window. Rebecca was so friendly and responsive and included lots of little touches that were very thoughtful.

Top guest favourite

Cabin in Saugerties

5 out of 5 average rating, 35 reviews

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars3 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

Guest favourite

Home in Salisbury

4.93 out of 5 average rating, 14 reviews

Stylish getaway in the Berkshires

NedRating, 5 stars1 week ago

Bright, light good layout inside and short walk to Salisbury and very short drive to Lakeville. Would definitely stay here again

Guest favourite

Home in Kent

4.97 out of 5 average rating, 36 reviews

Charming Home in Kent

RobertRating, 5 stars3 weeks ago

I was attending a blacksmithing conference at CAMA and the Slone museum. It was close by and an easy drive to the site. The house was very comfortable and well appointed. There are not many lodging options in Kent and this house solved that issue. I would whole heartedly recommend this property.

Cottage in Sharon

4.73 out of 5 average rating, 241 reviews

Rural small cabin with river view and access.

ScotRating, 5 stars4 days ago

We (my wife and I) chose this place because we wanted to get away to someplace beautiful for a personal / private retreat. Bill's place gave us everything we were hoping for. Privacy, near water / river, away from busy-ness, but not too far from home. A place we could turn off phones and computers, and read, write, talk, and reflect. Also, I must say the Bill is great with communication, and made check in easy. The day we checked in was very hot, and this being a "cabin in the woods", I wondered how hot it would be inside and how long it would take to cool down. It may seem trivial, but we walked in and the a/c's were on and it was SO refreshing...we immediately felt comfortable and happy with where we were. Sometimes it's the "little" things! Bottom line, the cabin is great, clean and comfortable. Having the Housatonic River right outside your front door is awesome. Thanks so much for delivering exactly what we needed. Highly recommended! Thank you Bill, Scot and Shelley

Top guest favourite

Home in Lakeville

5 out of 5 average rating, 15 reviews

Casa de campo: country escape

WendyRating, 5 stars5 days ago

This lake home is a lovely gem nestled inside a carefully landscaped floral paradise outside. The occasional creak in the wood floors as you walk from room to room gives it a charming air, while you have all the amenities you need to make your stay comfortable: modern kitchen and bathrooms, comfortable beds, ample seating throughout the home, and even fairy lights on the back deck! The neighborhood was quiet and peaceful, and just around the corner from restaurants and a grocery store. Great location! It was perfect for us while we were in town for a wedding. Thanks!!

Guest favourite