Vacation rentals in Twin Lakes

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Top-rated vacation rentals in Twin Lakes

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Guest favorite

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

4.93 out of 5 average rating, 108 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

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

Chalet in Otis

4.94 out of 5 average rating, 418 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favorite

A bright and airy living space features a round wooden dining table surrounded by black chairs. Large windows invite natural light, offering views of the scenic outdoor landscape. A seating area with a black sofa is positioned beside a modern fireplace, enhancing the room's comfort.

Apartment in Copake Falls

4.9 out of 5 average rating, 334 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Top guest favorite

Guesthouse in Millerton

4.98 out of 5 average rating, 105 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 favorite

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

4.99 out of 5 average rating, 144 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 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

5 out of 5 average rating, 367 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 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

4.92 out of 5 average rating, 157 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 favorite

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

Top guest favorite

Large windows frame a view of vibrant autumn foliage, with shades of green and gold visible in the trees outside. Two stylish chairs are positioned in front of the windows, inviting relaxation while enjoying the scenic landscape.

Bungalow in Cairo

4.99 out of 5 average rating, 441 reviews

Riverfront-swim & float the river-20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

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, 109 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 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

4.96 out of 5 average rating, 335 reviews

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!

Top guest favorite

A wooden serving tray displays a loaf of freshly baked bread alongside a bunch of bananas. A cup is partially visible, suggesting a beverage, while eggs rest in a pink bowl nearby. The table is made of natural wood, showcasing its unique grain patterns.

Treehouse in Wallkill

4.99 out of 5 average rating, 317 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Vacation rentals for every style

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Popular amenities for Twin Lakes vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Twin Lakes

Guest favorite

A wooden fence runs along a grassy area in the foreground, framed by soft mist. A colorful sunrise is visible in the sky, showcasing shades of pink and orange. Rolling hills are faintly outlined in the distance, partially obscured by fog.

Barn in Pine Plains

4.93 out of 5 average rating, 15 reviews

Stunning horse farm apt, hot tub

RicardoRating, 5 stars2 weeks ago

Wonderful get away! The apartment was great. Loved the pool table and the piano. The high ceilings is what makes the place so peaceful. Our kids loved watching the horses and the chickens. The pool is an added plus. Christine and Michael were very attentive. Highly recommend it.

Top guest favorite

A spiral staircase features rustic wooden railings and steps, surrounded by log walls. Natural light filters through the large windows, illuminating the inviting space. The design showcases the cabin's craftsmanship and connects the levels for easy access.

Cabin in Sheffield

5 out of 5 average rating, 29 reviews

Berkshires Cabin with Stunning Views

KamronRating, 5 stars1 week ago

Amazing place, incredibly clean & an even more incredible view. Loved it!

Superhost

An aerial view captures the rustic charm of the rebuilt hay barn surrounded by lush greenery and vibrant autumn foliage. A circular driveway leads up to the home, which is framed by trees and grass, showcasing the scenic marshland beyond.

Home in Salisbury

4.95 out of 5 average rating, 99 reviews

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

SethRating, 5 stars1 month ago

Very comfortable house - nice and airy. Great location just outside Lakeville. Highly recommend.

Guest favorite

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

4.91 out of 5 average rating, 23 reviews

Historical Falls Village Schoolhouse

HalRating, 5 stars3 weeks ago

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

Top guest favorite

An A-frame cabin is illuminated at night, featuring warm string lights adorning its exterior. A wooden deck extends from the cabin, accompanied by a picnic table positioned on the ground level. The surrounding environment exhibits a tranquil forest ambiance.

Cabin in Becket

5 out of 5 average rating, 7 reviews

WALK to lake! Dog friendly, A-Frame in Berkshires!

RicardaRating, 5 stars1 day ago

We had a great time in the lake cabin. It’s really well equipped and thoughtfully put together. We felt welcome and at home. Great hiking nearby, we used the fire pit and grill. House was easy to cool and the kitchen has all the essentials and then some. (We also loved our breakfast at the Neon Newt) thanks Nicole and Aaron!!

Top guest favorite

A newly built cabin is highlighted, featuring a classic design with natural wood siding. The property is surrounded by trees, and a stone walkway leads to the entrance. Soft evening light emanates from the windows, complementing the tranquil outdoor setting.

Home in East Jewett

4.98 out of 5 average rating, 42 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

JennRating, 5 stars3 days ago

Lovely stay! The place was spotless, beautifully decorated, and clearly designed with care. Everything felt thoughtfully chosen, and the amenities were great—comfortable bedding, quality toiletries, and a well-stocked kitchen. Would definitely stay here again!

Top guest favorite

Home in Sharon

5 out of 5 average rating, 28 reviews

Nature lover’s retreat in NWCT, breathtaking views

NaoRating, 5 stars1 day ago

Samantha & Kellen were amazing hosts and their place was so lovely!!! The house was even better than the photos - everything was clean, amenities were great, kitchen was well-stocked w/ tons of plates/cups/pots/pans, and most of all, the view was breathtaking - all you see is mountains and trees!! Can't think of anything that could've been improved! As the house is in the mountains & we went during a particularly high-tick season after lots of rain, our dog picked up a decent amount of ticks walking outside the property. Samantha & Kellen were super responsive and helpful, and went out of their way to get the tick sprayer & lawn mowers come out during our week-long stay. Would love to come back!!!

Top guest favorite