Bed and breakfast holiday rentals in Litchfield County

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Top-rated bed and breakfast rentals in Litchfield County

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Private room

4.9 out of 5 average rating, 39 reviews

Small Private Room w/ Bath

Sleep, Create, Rehearse!! We are located on nine wooded acres at the foothills of the Berskhire Mountains and surrounded by state parks (Kent Falls, Macedonia State Park and more!), private schools, and the Appalachian Trail. We're a short distance from three traditional New England covered bridges and just three miles from the charming town of Kent, an enchanting travel destination situated beside the Housatonic River. You can stroll around town and take advantage of Kent's great restaurants, galleries and shopping. We provide internet and breakfast, along with two loving dogs and two evil parrots. If you're hiking the Appalachian Trail, we will provide transportation to the trail head. A perfect escape from the city, only two hours away. If you don't have a car, and we're available, we can pick you up and deliver you from the Harlem Valley/Wingdale station on the Metro-North Line. Our fee for this service is $40 round trip, to be paid on arrival. We offer our home as a place to come and unwind. There are so many things to do but if you want to just sit in the sun and read that’s fine too. We have wi-fi and if you have work to do there are plenty of tables on which to set up your computer. There is an art studio you can work in. Just bring your supplies or, if you want, you’re welcome to use my potter’s wheels and and there is clay you can purchase from me. We have hiking trails all around the house. If you have a car the state park is just a few minutes down the road. There are great biking roads and the rail trail isn’t too far away. There are wonderful new restaurants in Kent and sweet little shops for clothing, art and crafts. There is a coffee and chocolate shop with outdoor tables - just perfect for people watching. There are a couple of wineries that are fairly close You may see us around, but the house is large enough to get lost in. On warm days you can have breakfast on the screened-in porch. It's on the second floor so you'll feel like you’re in the trees canopy with lots of birds to watch. Breakfast items will be provided, i.e. cereal, fruit, toast, etc. Coffee and tea are included. We also have an additional building of 3400 sq. ft. which houses a pottery and art studio and can also be used as a rehearsal space (theater, music, lecture hall, etc.) Please call or email for hall rental pricing. We must have adequate verification, including a phone call through airbnb. This is a basement room. There some wonderful restaurants in the area. A light breakfast will be available, but the kitchen will not be available for cooking dinner.

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Hotel room

Kennedy Suite - Homestead Inn

Feel Presidential for the night at the Homestead Inn. Stay in the room occupied by Joe and Rose Kennedy while JFK was attending Canterbury School in New Milford, CT circa 1930. Decorated with mahogany furnishings and unique memorabilia from JFK's family history and time at Canterbury. Presidential class amenities await you such as a jetted soaking tub that comfortably fits 2 and inclusive of a gourmet breakfast for 2. Nestled in the picturesque Housatonic Valley, in the town of New Milford, CT

Guest favourite

Private room

4.97 out of 5 average rating, 39 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, free wi-fi, a lovely shared bath with claw-foot tub, and a decorative fireplace. You will enjoy a shared wrap around open porch overlooking mature gardens, and a cozy second floor sun porch with sunset views.

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Hotel room

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

4.89 out of 5 average rating, 242 reviews

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

A completely renovated farmhouse ( formally a parsonage) built in 1900. 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.

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Private room

C5 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.

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Private room

C14 Carriage House at Blackberry River Inn

Superhost

Private room

C8 Carriage House at Blackberry River Inn

Guest favourite

Private room

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.

Guest favourite

Private room

4.88 out of 5 average rating, 58 reviews

PrivateRoom/Sunny/Clean/Peace/SelfCheckIn

A sunny clean second fl room with full size soft bed in a contemporary owner occupied single-family house, charming garden, 2h NYC/Boston, 35min Hartford, 1h Berkshire MA, 8 minutes golf/tennis court 30min Ski area. Self-check-in. There are some packed wood floor in the closet. 400+ thread count cotton bedding FULL size SOFT mattress Required shoes off No pets allowed No smoking permitted No service animals due to allergies and lack of experience Parties upon requesting

Private room

4.91 out of 5 average rating, 98 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.

Guest favourite

Private room

4.98 out of 5 average rating, 40 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.