Pet-friendly vacation rentals in Sharon

4.93 out of 5 average rating, 110 reviews

Apartment in Amenia

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.

4.89 out of 5 average rating, 157 reviews

Cabin in Salisbury

Cabin Nestled in the Litchfield Hills

Cozy, curated cabin in NW Connecticut—just over 2 hrs from NYC by car or train. Nestled above the Housatonic River, it’s a place to hike, antique, or do nothing at all. Watch wild turkeys, deer, rabbits, and the occasional fox wander through the yard. Toast s’mores by the fire pit, then stargaze beneath a wide, quiet sky. The Appalachian Trail and some of the best hikes in the Northeast are just steps away. A peaceful escape in every season—recharge with nature, friends, or the stillness itself.

4.83 out of 5 average rating, 102 reviews

Home in Cornwall

State Forest Getaway

Enjoy our Mountain getaway for year round fun! There are lots of activities close by-Mohawk Ski Mountain, Indian Lake and historic Covered Bridges! Hike in the backyard, cool off in the creek or relax in front of the Wood-burning fireplace or get the whole family together for a fun BBQ on the outdoor deck. We have 4 comfortable bedrooms plus daybed room and 3 bathrooms and a fully equipped Chefs Kitchen. The living room is great for lounging and perfect a movie night watched on the projector

4.96 out of 5 average rating, 361 reviews

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

4.95 out of 5 average rating, 177 reviews

Cabin in Cornwall

Vibrant, secluded dome home in Litchfield County!

Positive vibes, tranquility and refuge await! Reconnect with nature at this unforgettable escape on 3+ acres. Allowing an open flow of light, atmosphere, and energy, dome homes can offer a spiritual experience, and this property offers all that times two. Consider these naturally efficient domes your break from it all 10 minutes or less to; Skiing (Mohawk Mt.) Lake Waramaug Appalachian Trail Housatonic River Ct Wine Trail Kent Falls Antiques, art galleries, farmers markets, brewery, & more

4.95 out of 5 average rating, 100 reviews

Home in Salisbury

The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski

Newly Renovated 1890s Hay Barn. 3 Queen sized Beds on 2 floors w/ scenic marsh views. 3 min. from Millerton, lakes & Hotchkiss. Open loft spaces . Fully equiped kitchen. Ideal for couple or w/guests. Single Bathroom on Ground Floor. Full Music Set up w/ instruments and PA. Radiant floors, plus pellet stove for ambiance & additional heat. Wifi thermostat and smart lighting w/ Alexa. 42" TV with Firestick and cable. Full house Auto-Backup Generator. Rental car can be available with property.

4.98 out of 5 average rating, 194 reviews

Apartment in Pine Plains

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

4.92 out of 5 average rating, 416 reviews

Home in Millerton

Deluxe Mountaintop Skyloft,Forest,Views,Birds,WiFi

Atop Silver Mountain, outdoor living in the private forest overlooking the Hudson Valley. Enjoy nature with 200+ bird species, yoga, meditation, or quiet reading in the fresh, crisp mountain air Revel in privacy and tranquility, yet stay connected with 500Mbps WiFi, a 60” HD TV and wood burning fire stove. Unwind on a huge deck with cushioned chaise lounges for stargazing and Bar BQ Grill. Enjoy picnics by the private pond, deck, chaise lounges, a dock, paddle boat, fishing and fire-pit!

4.93 out of 5 average rating, 161 reviews

Cottage in Cornwall

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.

4.92 out of 5 average rating, 160 reviews

Home in Sharon

Nature Cottage w/ Private Path to River Access

Summertime in beautiful Sharon! Comfortable, rustic cottage with fire-pit, wood-burning stove, large deck for star-gazing, 4 acres, a brook and private path to 200' Housatonic River frontage. So cozy! In lovely Litchfield Hills, covered bridges, lake swimming, restaurants, the Appalachian trail and hiking trails, ski areas, Audubon Center, Clarke Outdoors tubing/ kayaking and Ellsworth Farms fruit picking. Near Millerton, Kent, Great Barrington. Lake beach pass included in the rental.

4.98 out of 5 average rating, 131 reviews

Home in Salisbury

Upland Meadow Retreat - 3 bedrooms/2 baths

Very comfortable 2000 square foot ranch home - 3 bedrooms, 2 bathrooms on 2 acres is the perfect getaway for a quiet relaxing time in the country. Our house is a few minutes from Hotchkiss, Salisbury and Indian Mountain Schools - and is close to town. This is quintessential New England at its best. Enjoy a perfect country setting offering peace and quiet in a beautiful, natural environment. Easy drive from New York/Boston, close to Metro North Wassaic train station.