Guesthouse vacation rentals in Litchfield County

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Top-rated guesthouse rentals in Litchfield County

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

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Superhost

Guesthouse in Winchester

4.97 out of 5 average rating, 59 reviews

Year-round Lakefront Highland Lake - Immaculate

"Lone Pine Cottage" Very special 3 bedroom / 2 full bath, 2016 ground-up restoration in Victorian cottage style. Magnificent in all four seasons. Desired direct waterfront spot on quiet east side cove. Perfect for couples or families. Kayaks, Canoe, sailboat. Central air, radiant heated floors, gas fireplace, washer/dryer, large deck with gas grill. Lawn area, good swimming area and dockage for you boat in front of the cottage. Strict no-pet and no-smoking inside the cottage policy

Aug 30 – Sep 6

R6,721 ZAR per night

Guest favorite

Guesthouse in Millerton

4.97 out of 5 average rating, 79 reviews

Loft in the Pines

Loft in the Pines: Get away to your own private retreat, walkable to Main St, Millerton, NY and Harlem Valley Rail Trail. Beautiful 1 bedroom escape with two decks for your relaxation. Perfect for couples or families. Close to great hiking and skiing. Easy walk to antique shops, the Music Cellar and delicious restaurants or put your feet up and relax! There are 1.5 baths, a living room with flat screen TV, dining room and a fully equipped kitchen with an expansive deck to take in the view.

Jan 27 – Feb 3

R2,864 ZAR per night

Guest favorite

Guesthouse in Litchfield

5.0 out of 5 average rating, 14 reviews

Bantam Woods Retreat - 2 bedrooms with queen beds

Brand new stand alone guest house. Nestled in the six acre woods, river frontage. Near downtown Bantam. Near Taft, Kent, Gunn, Rumsey Hall, Forman schools, great restaurants (Arethusa, Materia), shopping, galleries, antique shops. Hike at White Memorial, Hidden Valley Preserve, Mt. Tom. From Lynda: "Laurie’s stand-alone guest house was impeccable. Felt like we were the first ones to stay. Top quality appointments, serene setting. Just what the Dr ordered. We will return for sure. Super host".

Sep 26 – Oct 3

R4,295 ZAR per night

Guest favorite

Guesthouse in Washington

5.0 out of 5 average rating, 16 reviews

Private, cozy woodland getaway.

Perched atop a hill and surrounded by woodland, The Cabin is a secluded getaway that offers all the modern comforts required for a truly restorative stay. With its own yard, driveway, fireplace and private woodland trail, this cozy cottage for two is perfect for an escape in any season. Easy access to skiing, water sports on nearby lakes and miles upon miles of hiking trails. Expect to spot abundant wildlife! Bustling nearby villages offer plenty of cultural, dining and shopping opportunities.

May 9 – 16

R3,900 ZAR per night

Guest favorite

Guesthouse in Roxbury

5.0 out of 5 average rating, 15 reviews

Modern Country

Escape to a serene getaway in nature. Modern Country is a one bedroom guest house recently renovated by renowned European designers. This luxurious home boasts floor to ceiling windows allowing for unobstructed views of the surrounding Connecticut forest. Enjoy a glass of wine or complimentary Nespresso at the dining table while overlooking our private pond, or walk down the stone path to our outdoor retreat—complete with a hammock and fire pit—and take in the sounds of the running stream.

Jan 10 – 17

R4,576 ZAR per night

Guest favorite

Guesthouse in New Milford

5.0 out of 5 average rating, 43 reviews

Luxury in the Litchfield Hills

Enjoy this gut-renovated two-floor post-and-beam luxury cottage just outside Kent, CT. Just 9 minutes from downtown Kent and close to the best of Litchfield County, our cottage sits on a serene 3.5 acre property that backs up to protected woodlands. We painstakingly brought the rustic space into the present, with a new kitchenette; bathroom with a massive, spa-like shower; new HVAC; and hotel-like accommodations. Close to Kent School, Canterbury, and great for a romantic getaway.

Oct 9 – 16

R4,028 ZAR per night

Guest favorite

Guesthouse in Brookfield

4.82 out of 5 average rating, 39 reviews

The Greenhouse Oasis

Welcome to our eco-friendly modern greenhouse, a unique, architect-designed studio set on 2 acres of gardens & woods, just 1.5 hrs from NYC, and a mile from a lake & hiking in the rolling hills of Western CT. Here you'll find serenity, light, and space to relax, work or play. A great romantic getaway for couples or a restful abode for singles or professionals visiting/working in the area, this soaring, comfortable space is all yours − with private entrance, deck and more!

May 27 – Jun 3

R2,321 ZAR per night

Superhost

Guesthouse in Salisbury

4.89 out of 5 average rating, 91 reviews

Lakeville Studio, 1st floor Near Lake, Limerock

Cozy convenience in the center of Lakeville! Short walk to convenience store, several restaurants, a nail salon, gym and package store. There is a laundromat nearby as well. 1/2 mile to Lake Wonoscopomuc, nearby park and tennis courts, and beautiful walks on rural roads. Very close to local boarding schools and Limerock Racetrack. There are 2 units in this building- this listing is the downstairs only, there is a shared entrance, but units are separate of each other.

Jul 28 – Aug 4

R2,612 ZAR per night

Guesthouse in Litchfield

5.0 out of 5 average rating, 4 reviews

The Blacksmith Cottage

Stay in our cozy private 2 bed/2 bath guest cottage located in what was originally a blacksmith’s shop connected to the back of our 253 year old home on a few serene acres. Fully remodeled and updated this year. We are located minutes from the center of Bantam and a mile down the road from Bantam Lake, 20 minutes from Mohawk Mountain. Grab coffee at Arethusa and dinner at Materia, take a hike in White Memorial or Steep Rock, Check out Kent Falls in between.

Dec 17 – 24

R3,034 ZAR per night

Guest favorite

Guesthouse in Sharon

5.0 out of 5 average rating, 65 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.

Sep 15 – 22

R2,092 ZAR per night

Guest favorite

Guesthouse in Morris

4.94 out of 5 average rating, 34 reviews

Peaceful Year Round Lakehouse

Kick back and relax in this calm, stylish space. Bantam Lake Gem; private walk in beach with kayaks, fishing poles and floats. 2 story open floor plan. 2 bedrooms/1 bath. Large beautiful deck. Countless hiking trails. Town of Litchfield Connecticut, plenty of eateries, county fairs etc. Beautiful western exposure, picture perfect sunsets all year round Ice fishing 🎣 in the winter, nearby ski slopes ⛷, concert venues, breweries and shopping

Feb 16 – 23

R5,282 ZAR per night

Guesthouse in Morris

5.0 out of 5 average rating, 4 reviews

Treehouse on Bantam Lake!

Come stay at this relaxing and tranquil getaway. Located on Bantam Lake with lake front access. Enjoy the beauty of lake views, sunsets, sunrises, tennis and pickle ball courts, close to many hiking trails as well as the lovely towns of Bantam and Litchfield with their excellent restaurants, markets and fun stores. We are located close to many boarding schools... Rumsey Hall, Taft, The Fredrick Gunn school and Foreman.

Apr 4 – 11

R5,528 ZAR per night