Bed and breakfast vacation rentals in Chelmsford

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Top-rated bed and breakfast rentals in Chelmsford

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

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Top guest favorite
Private room in Fenway-Kenmore
4.94 out of 5 average rating, 366 reviews

Fenway Park Vintage Brownstone (4C)

This charming brownstone, built in 1896, is set on quiet, tree-lined Bay State road, one of the "10 Boston’s Best Secret Streets" by Travel and Leisure. It is under the Boston landmark Citgo Sign, within 5 minute walking distance to Fenway Park, Kenmore Sq, Charles River and Boston University. The property has been lovingly maintained as a private residence for two generations. All original architectural details have been preserved with Victorian charm. Guest rooms are on the 3rd or 4th floor.

Guest favorite
A cozy guest room features warm orange walls, a queen-sized bed with white linens, and decorative pillows. A workspace with a desk and chair is positioned by a window, which allows natural light. A patterned area rug adds comfort to the hardwood floor.
Private room in Quincy
4.87 out of 5 average rating, 157 reviews

Room with private 1/2 bath, a few 5 min walk to T

Top Choice Homestay! Our meticulously crafted guest rooms are certain to meet all your expectations. Located in Quincy Center, you'll find the subway, train station, buses, supermarkets, banks, and delectable dining options all just steps away! Boston's major attractions and the scholarly charm of universities are conveniently within the reach of the Red Line subway. Start your mornings with our invigorating self-serve breakfast, infusing your day with vitality. We look forward to your visit.

Top guest favorite
The exterior of a red house is framed by a well-maintained garden comprising various flowers and greenery. The house features a welcoming entryway, a chimney, and a grassy area. Sunlight illuminates the scene, highlighting the vibrant colors of the surrounding landscape.
Apartment in Dedham
4.94 out of 5 average rating, 214 reviews

Two bedrooms, full bathroom, and breakfast room

We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

Top guest favorite
The logo of Kiss Flower Farm features a hummingbird approaching a delicate flower set against a soft, pastel background. The name 'Kiss Flower Farm' is elegantly inscribed in a circular format, enhancing the farm's identity.
Private room in Norwell
4.88 out of 5 average rating, 453 reviews

Kiss Flower Farm

Kiss Flower Farm is a bnb and specialty foods purveyor, located in a quaint 1876 New England farmhouse. Abundant with herb and flower gardens sprawling alongside a classic horse barn, our farm has charmed guests from over 20 countries since 2013. Our private guest quarters make for peaceful stay, and our made-from-scratch breakfasts bring a delicious start to your morning. The farm’s close proximity to natural and cultural attractions also offers many options for exploration and adventure.

Top guest favorite
Private room in York
4.96 out of 5 average rating, 590 reviews

Ogunquit Tranquil Setting near Perkins Cove

Summer Weekend Booking Policy (June–August): To ensure fair availability during our busiest season, weekend stays must include Friday and Saturday nights. Thursday bookings must include Friday and Saturday Sunday bookings must include Friday or Saturday Friday–Saturday stays are always welcome We appreciate your understanding and look forward to hosting you in our peaceful Ogunquit retreat. Private entrance with patio. A nicely appointed suite with a luxury queen bed.

Top guest favorite
A well-lit queen bedroom features a plush bed with a decorative blanket and a soft throw. Two windows adorned with light curtains allow natural light to fill the room, while soft colors on the walls create a calming atmosphere. A framed art piece is visible on the wall.
Private room in Watertown
5 out of 5 average rating, 109 reviews

Private living/dining/ kitchenette - Treetop Suite

Your private guest suite features one queen bedroom, full bath, living room, kitchenette, and dining area, all located on the entire third floor of our home. Once you enter through our home and close the door to the third floor, you'll be amazed at how separate you'll feel. We're situated in a quiet neighborhood, yet only a 7-minute walk to the bus or train into Boston. Curl up with a cup of tea in the evening and enjoy a light breakfast in the morning. We would love to host you!

Top guest favorite
Private room in Marshfield
4.96 out of 5 average rating, 333 reviews

Peaceful by the Sea with breakfast (1 of 2 rooms)

PEACEFUL ROOM is appropriately named as peace and quiet is most important when hosting guests. It comes with A FULL BREAKFAST that is served at 8-8:30 AM. It is a 5 minute walk to an array of restaurants, beaches, ice cream store, groceries, nail salon, clothing shop, as well as a souvenir shop and more. Going for a bike ride, jog or a walk, this is your spot! There is also pickle ball within a 10 minute walk. There is very little use of the fridge and no cooking is allowed.

Top guest favorite
Home in Antrim
4.98 out of 5 average rating, 232 reviews

HotTub FirePit Games Huge Backyard Family Friendly

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

Guest favorite
Private room in Medford
4.86 out of 5 average rating, 105 reviews

Grand Victorian gets Contemporary Facelift! #1

Our home is a rather unique and very updated 100+ year old Victorian in a historic neighborhood in Medford. There is convenient access to Boston either by car or by public transportation. We hope you'll enjoy the comfy queen sleigh bed, large open dresser, and loads of other amenities our home provides. While we do offer various teas and coffee to our guests, we don’t offer breakfast or food items generally. But you may use the kitchen if you so choose!

Top guest favorite
A private deck features a hot tub beside a wooden seating area with four chairs arranged around a fire pit. A blue umbrella provides shade, while cozy bathrobes hang on the fence, inviting relaxation in the natural surroundings.
Guest suite in New Boston
4.99 out of 5 average rating, 222 reviews

Private Suite with Hot Tub

#BarnQuiltHouse Cozy, private guest suite with hot tub in the wooded hills of a quaint New Hampshire farming town. Residential neighborhood, centrally located in Southern New Hampshire. 20+/-min to Concord, Manchester Airport, St. Anselms College, New England College, Pat's Peak, Crotched Mountain. Head north to the lakes region, west to Mt. Sunapee, or south to visit Boston..all within an hour+ drive. May the peace of the wilderness be with you.

Top guest favorite
A cozy living space features exposed wooden beams and wide pine flooring. A comfortable sofa is placed beside a coffee table, while a television is mounted above a brick fireplace. Natural light fills the room through multiple windows, enhancing the inviting ambiance.
Apartment in York
4.98 out of 5 average rating, 342 reviews

History Steps from the Beach

If you’re looking for more space and amenities than staying in a hotel room, but still want the cleanliness and professionalism you’d expect from one, then you may enjoy staying here. Our spacious 3 room, 1,200 square foot historic (c. 1670) one bedroom apartment for two guests has exposed beams, wide pine floors, full bath, kitchenette, and is just a short walk to Long Sands Beach or a short drive to York Beach, York Harbor, or York Village.

Guest favorite
A spacious bedroom features a four-poster bed adorned with decorative pillows and a patterned throw. Natural light enters through two large windows, illuminating the hardwood floor and side tables. Floral curtains and framed artwork add a touch of color to the inviting atmosphere.
Private room in Dorchester
4.96 out of 5 average rating, 339 reviews

Large Private room in Savin Hill

My place is close to Malibu and Savin Hill Beaches. You’ll love my place because of the neighborhood, and the coziness. This is an old Boston home. We are close to the T, easily accessible from Logan airport. Just a few stops from downtown Boston. My place is good for solo adventurers and business travelers, medical people. All walks of life welcome here. Registered with the City of Boston #STR383505

Popular amenities for Chelmsford bed and breakfast rentals

When is the best time to visit Chelmsford?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$9,624 GYDG$9,624 GYDG$11,507 GYDG$12,553 GYDG$11,716 GYDG$12,762 GYDG$14,436 GYDG$11,716 GYDG$11,507 GYDG$11,507 GYDG$10,879 GYDG$9,624 GYD
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Quick stats about bed and breakfast rentals in Chelmsford

  • Total vacation rentals

    Explore 20 vacation rentals in Chelmsford

  • Nightly prices starting at

    Chelmsford vacation rentals start at G$10,461 GYD per night before taxes and fees

  • Verified guest reviews

    Over 510 verified reviews to help you choose

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chelmsford vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chelmsford rentals

  • 4.9 Average rating

    Chelmsford stays are highly rated by guests—averaging 4.9 out of 5!