Vacation rentals in Lakeville, Salisbury

4.92 out of 5 average rating, 106 reviews

A covered front porch features wooden flooring and is framed by dark columns. Two rustic wooden chairs are positioned beside a small table, creating a space for relaxation. Surrounding greenery is visible, enhancing the natural setting.

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.

4.95 out of 5 average rating, 105 reviews

A bathroom is depicted, featuring a bathtub surrounded by white tiles. A shower curtain is pulled to the side, allowing light to enter through a small window above. A white toilet is positioned nearby, and soft towels are neatly arranged in a wicker basket.

Guesthouse in Salisbury

Lakeville studio, 2nd floor Near Lake, Limerock AT

Spacious second floor studio. Close to local private schools, Catamount and Butternut ski areas, Limerock park, nearby Berkshires attractions, ski jumps! Short walk to convenience store, several restaurants, a nail salon, gym and package store. There is a laundromat nearby. 1/2 mile to Lake Wonoscopomuc, nearby park and tennis courts, and beautiful walks on rural roads. There are 2 units in this building- this listing is the upstairs, shared entrance but units are separate of each other. Edit

4.98 out of 5 average rating, 104 reviews

Guesthouse in Millerton

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

4.98 out of 5 average rating, 183 reviews

A kitchen area is presented, featuring a microwave and convection oven on a shelf. Blue dishware is arranged above, while cooking utensils hang to the left. A lower shelf holds additional kitchen items. The wall is painted a soft yellow, contributing to a bright environment.

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.

4.99 out of 5 average rating, 144 reviews

A winter scene is depicted with a red building contrasting against a vibrant sunset sky, filled with shades of orange and pink. Snow covers the ground and rooftops. Dark trees frame the image, contributing to the serene atmosphere.

Apartment in Canaan

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

5 out of 5 average rating, 366 reviews

A wooden bowl filled with various eggs sits on a wooden countertop next to a white microwave. A green ceramic pitcher filled with vibrant yellow daffodils adds a fresh touch to the space.

Apartment in Sheffield

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

4.92 out of 5 average rating, 156 reviews

A modern kitchen features white marble countertops and stainless steel appliances, including a gas stove and coffee maker. Skylights provide natural light, while open shelving showcases plants. Two black bar stools are positioned at the island, and a round dining table is visible in the foreground.

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.

Superhost

A modern bathroom is featured, showcasing a walk-in shower with a glass enclosure. A sleek vanity with a dark wooden base holds a white sink. Above, a round mirror is mounted on the wall. Geometric floor tiles add visual interest, complemented by a black shower fixture.

Apartment in Millerton

4.79 out of 5 average rating, 108 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.

4.98 out of 5 average rating, 129 reviews

A spacious wooden deck is surrounded by greenery, featuring a white lounge chair positioned for relaxation. A small table and decorative plant pots with flowers are visible, enhancing the natural setting. Sunlight filters through the trees, creating a serene outdoor space.

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.

4.93 out of 5 average rating, 368 reviews

Guest suite in Millerton

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.

4.86 out of 5 average rating, 155 reviews

A sunny view of the country cottage’s exterior showcases a large, grassy yard framed by a mature tree. The inviting porch features a couple of wooden chairs, while pastures and trees extend into the distance, creating a serene rural setting.

Cottage in North East

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!

4.96 out of 5 average rating, 335 reviews

A wooden sauna is showcased with glass doors, highlighting a spacious interior with wooden benches and a soothing blue light. Natural light filters in through a window, adding warmth to the inviting atmosphere.

Farm stay in Ancram

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

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Other great vacation rentals in Lakeville, Salisbury

Superhost

An aerial view captures the modern structure with large floor-to-ceiling windows, showcasing a warm glow from the interior lights. The building is surrounded by lush greenery and features a terrace adorned with chairs, providing expansive outdoor space for relaxation.

Home in Salisbury

5 out of 5 average rating, 3 reviews

Lakefront Escape | Private Dock Hot Tub & Views

ScottRating, 5 stars1 month ago

Although I had difficulty of checking in the house, my family had wonderful and happy memories ! I'll be back for sure!!! Thank you very much!^..^

4.91 out of 5 average rating, 23 reviews

Warm wooden walls and ceilings frame a cozy living area. A stone chimney features a wood-burning stove. Comfortable seating is grouped around a glass-top table. A dining space with wooden chairs and a kitchen area is visible in the background, illuminated by natural light.

Cottage in Canaan

Historical Falls Village Schoolhouse

HalRating, 5 stars2 weeks ago

Charming home, and Cath was especially helpful with late night dining accommodations.

5 out of 5 average rating, 22 reviews

Gorgeous Modern New Ranch near Rail Trail!

JonathanRating, 5 stars4 weeks ago

This is a great place. Peter is very responsive. The house is immaculate. Modern, clean and comfortable. The instructions are clear and everything is easy to use. The outdoor areas are really nice. It rained the whole time during our stay, but there is no mud and the covered front porch still gives you useable outdoor space. It is a short trip into Millerton where there are lots of great options to grab something to eat.

5 out of 5 average rating, 33 reviews

Modern Ranch Retreat in Hudson Valley

LisaRating, 5 stars1 week ago

Great location, walkable and bikable to town, and easy access to the Harlem Valley Rail Trail. The house was immaculate and a great size for our family (two adults and two kids 9 and 12). We would definitely stay here again if we return to the area.

Superhost

A private deck overlooks a lush, mostly wooded area with abundant greenery. Sunlight filters through the leaves, illuminating the natural landscape. A portion of the lawn is visible, enhancing the sense of seclusion and tranquility offered by the surroundings.

4.9 out of 5 average rating, 10 reviews

Private cabin on five acres close to town

EmilyRating, 5 stars3 months ago

Our group of 6 had a great time at PE's cabin! The place looks nice in pictures, but even better in person. It is uniquely decorated, cozy, and functional. We spent most of our time at skiing Catamount only 20 minutes away, so although had to squeeze a bit for sleeping (still comfortable, but had one guest sleeping on a floor mattress and another on the couch) this was still perfect for our needs as we could all comfortably hang out together in the living room! PE was always quick to answer any questions and gave clear instructions for how to check in. Overall a great place to stay.

A fire pit is centered between two wooden chairs on a grassy area, surrounded by a tranquil mountain landscape. The night sky is illuminated by a bright moon, creating a serene ambiance. A wooden deck is visible in the background, enhancing the outdoor experience.

4.97 out of 5 average rating, 33 reviews

Upstate NY - "MJ's Retreat"

AnkanRating, 5 stars2 weeks ago

This was my second time staying at MJ’s Retreat, and it was every bit as great as the first! Thanks (again) for a wonderful stay!

4.98 out of 5 average rating, 92 reviews

Cottage in Canaan

The Cottage at Great Falls Luxury Getaway.

ErinRating, 5 stars3 weeks ago

the cottage was gorgeous and everything we needed. the instructions to get in and where to find everything were very clear. I loved the guest book with local information and recommendations! we would definitely stay again!