Vacation rentals in Lakeville

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Top-rated vacation rentals in Lakeville

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Guest favorite

A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.

Apartment in Amenia

4.93 out of 5 average rating, 119 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 favorite

A cozy living area showcases a mix of seating options, including two vibrant couches with decorative throws and cushions. A wooden coffee table is centered on a patterned rug, with a warm glow provided by a nearby lamp. Natural light enters through a window, highlighting the rustic wooden beams overhead.

Cabin in Salisbury

4.89 out of 5 average rating, 159 reviews

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.

Top guest favorite

An outdoor deck showcases a round table surrounded by three metal chairs. A small vase with white flowers is positioned at the center of the table. Lush greenery and tall trees provide a tranquil backdrop, with a partially cloudy sky overhead.

Guesthouse in Millerton

4.98 out of 5 average rating, 111 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

Guest favorite

An open loft space showcases bright white wooden floors and a beamed ceiling. A comfortable couch and a hammock chair are positioned among large windows, allowing natural light to fill the room. Potted plants add a touch of greenery, while a wooden coffee table anchors the seating area.

Home in Lakeville

4.94 out of 5 average rating, 104 reviews

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.

Top guest favorite

The kitchen features modern white cabinetry with black handles, complemented by a light-colored countertop. A stainless steel sink is positioned under a wall-mounted faucet. A tile backsplash in neutral tones adds texture, while a fire extinguisher is mounted for safety.

Apartment in Pine Plains

4.98 out of 5 average rating, 211 reviews

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.

Top guest favorite

A newly remodeled kitchen showcases white cabinets complemented by a marble countertop and a decorative backsplash. A rustic wooden dining table with chairs is positioned near a window, while a vibrant area rug adds warmth to the space. Modern appliances are neatly integrated into the design.

Home in Salisbury

4.98 out of 5 average rating, 160 reviews

Under Mountain House

Our home is designed to be your home away from home! It has been newly renovated with comfort in mind so you can enjoy your stay in the Berkshires. Whether you are here to hike parts of the Appalachian Trail, stroll into town for a leisurely meal, enjoy Lime Rock Race Track or explore the many surrounding New England towns you can be assured you will always have a comfortable home to come back to!! My home is located just a 3 minute walk to the center of town and the historic White Hart.

Top guest favorite

The exterior of a two-story house is displayed, featuring a combination of white siding and a metal roof. An American flag hangs from the porch, surrounded by greenery and flower beds. The front pathway leads to a welcoming porch space.

Apartment in Canaan

4.99 out of 5 average rating, 156 reviews

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.

Top guest favorite

A spacious living area features comfortable seating, a glass coffee table, and a dining space with wooden chairs. The kitchen is visible, showcasing modern appliances and a light wood countertop. Natural light illuminates the room, creating a warm and open atmosphere.

Apartment in Sheffield

5 out of 5 average rating, 377 reviews

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.

Guest favorite

A modern black cottage is presented, set against a backdrop of tall trees and natural stone landscaping. A gravel driveway leads up to the entrance, where steps ascend to a covered porch. A dog is seen on the grassy area nearby.

Cottage in Cornwall

4.92 out of 5 average rating, 169 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.

Top guest favorite

A cozy living room features a large sectional sofa and an ornate ottoman at the center. A spacious TV unit stands against the far wall, complemented by natural light filtering through multiple windows. A bookshelf and decorative pieces enhance the inviting atmosphere.

Guest suite in Canaan

4.98 out of 5 average rating, 370 reviews

Stay in Downtown Canaan

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Guest favorite

A cozy sleeping area features a warm-toned bedspread draped over a spacious bed, complemented by accent pillows. A low bedside table holds a lamp, while a nearby chair adds additional seating. Green plants bring a touch of nature to the inviting space.

Apartment in Millerton

4.8 out of 5 average rating, 116 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.

Top guest favorite

A spacious living room features large windows allowing natural light to filter in. Comfortable sofas are arranged around a focal point gas fireplace, with a television nearby. A decorative rug enhances the warm ambiance, and double doors open to a wraparound deck.

Home in Lakeville

4.99 out of 5 average rating, 135 reviews

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.