Guesthouse vacation rentals in Litchfield County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Litchfield County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Rhinebeck

4.99 out of 5 average rating, 130 reviews

Country Suite Near Omega Inst and Rhinebeck

We designed our guesthouse with the comfort seeking guest in mind. Enjoy our extra comfy plush beds, soft and fresh bed linens, luxurious towels, and complimentary essential oil infused bath amenities for your ultimate getaway. Complimentary snack and beverage selections provided for your enjoyment in our efficient kitchenette which can accommodate light meals. Our second floor guesthouse offers a newly installed ductless HVAC to provide the ultimate comfort air-conditioning or heating as needed. Many of our guests comment on our relentless pursuit of cleanliness. Some features included are: kitchen with microwave, toaster oven, refrigerator/freezer, electric tea kettle, and Keurig coffee maker. Also, oversized shower, dimmable lighting, keyless access, internet, smart TV, blackout window treatments, heating and air conditioning. Kitchen is for light meal preparation only, no stove. Complimentary snacks, beverages, and bath amenities provided. Echo Dot with Amazon Alexa in suite for guest use. Please note: entrance includes one flight of stairs to enter and exit the country suite. Available promptly by Airbnb messaging, text or phone for any questions or needs during your stay. The guesthouse is within walking distance to the Omega Institute for Holistic Studies, 8 miles to the charming and historic town of Rhinebeck, and central to many pursuits in the Hudson Valley. Walk or run around the lake for a 3.5-mile outing. 90 miles from NYC along Taconic State Pkwy. 15 mins from Amtrak's Rhinecliff station. 25 mins from Metro North's Poughkeepsie station. Walk or run around the lake for a 3.5 mile outing. Our guesthouse is a separate structure from our main home on the property. Each building is separated by around 30 feet.

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 344 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

Guesthouse in Salisbury

4.95 out of 5 average rating, 108 reviews

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

Top guest favorite

Guesthouse in Millerton

4.98 out of 5 average rating, 109 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

Superhost

Guesthouse in Dover Plains

4.87 out of 5 average rating, 124 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 favorite

Guesthouse in Mahopac

4.95 out of 5 average rating, 252 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Guest favorite

Guesthouse in Brewster

4.94 out of 5 average rating, 153 reviews

Sherwood Barn - close to ski mountain

Our guests stay on the SECOND floor of the barn in a 1200 Sq Ft, fully reno'd apt that sleeps 6. Located about 1 hour from NYC you will find peace and serenity in the middle of nature on this 4 acre estate (that also contains our main home) where you can get away from it all. unwind this way or visit local attractions like Thunder Ridge Ski Mountain, snowshoe/ X Country skiing, hike/bike/running trails, restaurants and local cafe's. Great oasis to kick back and spend time with family.

Guest favorite

Guesthouse in Great Barrington

4.95 out of 5 average rating, 139 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Top guest favorite

Guesthouse in Wallingford

5 out of 5 average rating, 129 reviews

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Top guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 205 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Top guest favorite

Guesthouse in Sharon

4.94 out of 5 average rating, 124 reviews

Cottage with a Waterfall View

Fall asleep to the sound of a waterfall and babbling brook outside your bedroom window in this historic former flax mill known as St. John's Mill. The cottage is newly renovated and features a well equipped kitchen, sofa where you can put up your feet and gaze out the living room window at the dam and waterfall, and a private grill and terrace overlooking Guinea Creek. Located along a scenic route convenient to Kent, Millerton, Salisbury & Amenia.

Guest favorite

Guesthouse in New Haven

4.93 out of 5 average rating, 319 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.