Bed and breakfast holiday rentals in Litchfield County

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Top-rated bed and breakfasts in Litchfield County

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Superhost

Private room in Sandisfield

4.93 out of 5 average rating, 141 reviews

Hospitality in the Berkshire Woods

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light. Breakfast included!

Top Guest favourite

Private room in Norfolk

4.98 out of 5 average rating, 45 reviews

Maple House, Birch Room

Enjoy a relaxing visit to a romantic Victorian home. Located in the Berkshires village of Norfolk, a 2 minute walk from the Yale Summer School of Music and Art and music venue Infinity Hall, this classic features the Birch Room decorated with original watercolors, a new queen Leesa bed, high speed wi-fi, a lovely shared bath with claw-foot tub, and a decorative fireplace. You will enjoy a shared wrap around open porch overlooking the gardens, and a cozy second floor sun porch with sunset views.

Cabin in Sheffield

4.78 out of 5 average rating, 74 reviews

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

Guest favourite

Private room in Sheffield

4.98 out of 5 average rating, 50 reviews

Sheffield Lodge - Ramblewood Master

The Sheffield Lodge is a warm and inviting rustic Bed and Breakfast secluded from city life nestled in a pine forest. Enjoy your home-away-from-home where there is always friendly service, delicious breakfasts, afternoon treats. The lodge features an inviting fireplace, large screen TV, game table for board games or cards and a quiet reading/living room, and ample parking. Outdoor recreation is within minutes in every direction. There are museums, shops and many great restaurants nearby.

Superhost

Hotel room in New Milford

5 out of 5 average rating, 4 reviews

Marilyn Monroe Suite - Homestead Inn

Spend the night in the suite occupied by Marilyn Monroe. Marilyn was a frequent guest of the Homestead Inn while courting Arthur Miller in the neighboring town of Roxbury in the 1950's. Formerly Room 22, the Marilyn Suite is decorated in her favorite colors of alabaster and white. Tastefully finished with unique memorabilia and luxurious amenities such as a jacuzzi soaking tub. Nestled in the picturesque Housatonic Valley, in the quaint town of New Milford, CT - Gourmet Breakfast for 2!

Guest favourite

Private room in New Milford

4.91 out of 5 average rating, 299 reviews

"The Parsonage" 1 or 2 Bdrm Suite with full bath

A completely renovated farmhouse ( formally a parsonage) built in 1890. Beautifully landscaped gardens and sitting areas located in the backyard. Backyard amenities include a patio, fire pit, hammock and picnic table. Check in through front door ( shared by owner) to stairs leading to second floor to guest quarters, which include a Master BR, living room/dry kitchenette with mini fridge and large full bath. A 2nd bedroom is available at an additional cost of $30.00 per guest,per night.

Top Guest favourite

Private room in Brewster

4.96 out of 5 average rating, 48 reviews

Suite by the Lake, HudsonValley/ pets welcome.

Enjoy this stylish and unique place. The suite by the lake is a cozy getaway on the scenic banks of the Croton watershed. About 1 hour from NYC, it's in the main house, an 1850 farmhouse & has a kitchenette , bath and a working space area. It has a private entrance by the pool. The pool has a big seating and lounging area with tranquil views of the lake. The comfortable bed is a queen size. Shared spaces are only the outdoor areas ex.pool, vegetable garden, Zen garden, parking area.

Guest favourite

Private room in Goshen

4.93 out of 5 average rating, 30 reviews

Lake View Ridge Massage and Bed & Breakfast Rm. #1

Private home in small quaint village. Two bedrooms with SHARED DOUBLE SINK BATHROOM. Each room has a queen size bed with down comforter, feather bed and 6 pillows, desk, chair, closet and dresser. Amenities such as shampoo, soap, towels are included. Use of hot tub is open to guests evening hours from 7pm - 9pm. There is a $25.00 fee for use. A full DELUXE breakfast is provided each morning. Hot and cold beverages are offered at all times. House is very clean and comfortable.

Superhost

Private room in Norfolk

C1 Carriage House at Blackberry River Inn

The Blackberry River Inn is Bed & Breakfast, with the main house being a converted Colonial mansion built in 1763. The Inn lies nestled in the foothills of the Berkshire Mountains on 27 scenic acres. Breakfast is made-to-order and served in the dining room of the main house. In addition to the main house with its 2 deluxe rooms and 2 suites, the Inn includes the Carriage House with 12 rooms, the Cottage, and an outdoor swimming pool. The Inn is located in Norfolk, founded in 1758.

Guest favourite

Private room in Harwinton

4.87 out of 5 average rating, 69 reviews

PrivateRoom/Sunny/Clean/Peace/SelfCheckIn

A sunny clean second fl room in a contemporary owner occupied single-family house, charming garden, 2h NYC/Boston, 35min Hartford, 8 min golf course Self-check-in. cotton bedding FULL size SOFT mattress Required shoes off No pets allowed No smoking permitted No pets and service animals due to allergies and lack of experience Parties upon requesting A visible camera is installed in the shared kitchen not facing private areas. See "Safety" section for full details

Guest favourite

Private room in Goshen

4.91 out of 5 average rating, 99 reviews

Classic New England Bed & Breakfast

The Mary Stuart House Bed & Breakfast is located in the northwest corner of Connecticut in the heart of the Litchfield Hills. Owned and run by Mary Orlando, this recently restored 1798 historic colonial home has been in the family for over 65 years. Mary has been welcoming travelers and vacationers into her home since 1998. Open year round, this peaceful country setting, with its manicured lawns and gardens makes for a relaxing getaway.

Top Guest favourite

Private room in Roxbury

4.98 out of 5 average rating, 46 reviews

Mine Hill Getaway West Room

This property has two bedrooms on the 2nd floor which can be booked separately or together. The West Room is a sunny yellow, and also has two windows and a good view of the forest. The bathroom is en-suite. Guests may use the salt-water lap pool in the summer months and enjoy the garden. A light breakfast is offered. Note: There is no elevator. There is parking available on the driveway. Each bedroom has its own private bathroom.