Holiday houses in Chelmsford

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Top-rated holiday rentals in Chelmsford

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

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Top Guest favourite
An inviting open-concept living area features a brown sectional sofa with a chaise, accented by throw pillows. A round coffee table sits in front, surrounded by a welcoming atmosphere of honeybee-themed decor, such as hexagon shelves on the wall. A workspace with a chair is positioned nearby.
Apartment in Billerica
4.99 out of 5 average rating, 167 reviews

Air Bee-n-Bee Hive-Unique Themed Stay, Coffee bar

Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

Guest favourite
A living area is depicted featuring a gray couch with a chaise, complemented by decorative cushions. A vibrant piece of artwork is displayed above the couch, while a colorful stained glass window permits natural light. The floor showcases warm hardwood tones and a plush area rug.
Condo in North Chelmsford
4.85 out of 5 average rating, 33 reviews

Perfect getaway, enjoy the seasons!

Travelers Welcome! Just bring yourself. Each season, cozy up in this quaint space and slip on a plush robe with some slippers, which can be found onsite. We do have central ac! Located in the Historic town of North Chelmsford, a little more like “city life” during rush hour and on the weekends. 2-5 minutes in walking distance to so many spots- Restaurants, the lake, the park, the Merrimack River and 45 minute drive to Boston. I hope you agree this space is filled with peace and relaxation

Top Guest favourite
A spacious living area is presented with a comfortable sofa and an elegant armchair. A dark coffee table sits at the center, while a dining table is visible in the background. Natural light illuminates the room through the windows, enhancing the cozy atmosphere.
Apartment in Woburn
4.95 out of 5 average rating, 209 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

Guest favourite
A wooden staircase leads to a blue front door, framed by two hanging planters filled with vibrant flowers. A large, decorative white pot sits at the base, featuring a lush green plant surrounded by smaller potted plants, enhancing the entrance's welcoming appearance.
Condo in North Chelmsford
4.88 out of 5 average rating, 103 reviews

The Art Experience

The Art House at the Ellison Building was built in 1878. This unit was renovated in 2004 and 2022. It is walking distance to both Freeman lake beach and also a boat launch for the Merrimack River. It's situated between Lowell and Nashua NH. 40 minute drive to Boston or Manchester. This 2 bedroom condo was renovated by artist/architect Daniel Forcier. All of the artwork hanging is for sale and Daniel has his art studio on site where classes are available for the complete art experience.

Top Guest favourite
An open-concept living area is highlighted by hardwood floors and a vaulted ceiling. A maintenance-free reef tank with ambient lighting is displayed on the wall. Modern seating options include a sectional sofa and chairs arranged around a coffee table, with large windows providing natural light.
Apartment in Westford
4.94 out of 5 average rating, 121 reviews

Large One Bedroom Apartment

1,100 square feet, completely renovated, 1 bedroom with a walk-in closet. Large bathroom with two sinks and walk-in shower. Open concept living, dining and kitchen area with vaulted ceiling. Hardwood floors throughout. Central air. Apartment is connected to a main house but with no interior access between house and apartment whatsoever. (No interior connecting doors at all) It has its own private driveway and side yard. Reef tank will no longer be in the apartment after May 20th.

Guest favourite
A spacious studio bedroom features a metal frame bed with floral bedding. A sleek desk chair is positioned near a window, allowing natural light to fill the room. A wooden nightstand and decorative wall art add character, while a soft rug lies on the floor.
Apartment in Westford
5 out of 5 average rating, 21 reviews

Westford Woods Retreat

Perfect for a couple or single traveler, Westford Woods Retreat is a cozy place to be on a winter day! This centrally-located studio apartment is the place to stay when visiting the snowy mountains of New England. Nashoba Valley Ski Area is just 15 minutes away! Guests also have access to two sets of adult snow shoes with multiple snowshoeing trails within 15 minutes of the Airbnb. With a private entry to the 2nd floor, it's the perfect place to relax after a day of adventuring.

Top Guest favourite
A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.
Home in North Chelmsford
5 out of 5 average rating, 228 reviews

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Top Guest favourite
A spacious loft area features a queen-sized bed with a cozy comforter and decorative pillows, alongside a daybed for seating or lounging. Wooden beams and a rustic brick hearth enhance the charm. Light enters through multiple windows, illuminating the inviting space.
Guest suite in Littleton
4.91 out of 5 average rating, 442 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

Top Guest favourite
A cozy living area features a red sofa and a round wooden table with two chairs. A small bedside table is positioned nearby. The kitchen is visible with wooden cabinets and appliances, and natural light highlights the space through a skylight.
Apartment in Westford
4.92 out of 5 average rating, 84 reviews

Furnished Cozy Apartment in quiet neighborhood

Come stay in this great place with nice cozy apartment features in a quiet neighborhood. Are you looking to getaway for a few days, relax, rejuvenate and get back to your everyday hustle? Are you looking for a perfect place to work remotely at shoe string budget? Conveniently located this place offer these and more including recreational activities all year long - NE beaches in summer, fishing, leaf peeping in Fall, skiing in winter etc Close to UMass Lowell

Top Guest favourite
A charming guest house is shown with a welcoming wraparound porch, adorned with a striped awning. Lush green grass leads to the house, surrounded by trees and landscaped beds. A gravel path extends alongside, enhancing the outdoor space.
Barn in Acton
5 out of 5 average rating, 50 reviews

Hidden Gem

This memorable hidden gem in historical Acton, is anything but ordinary. With your own parking area and semi-private entrance this tastefully decorated guest house is close to many hot spots. The Bruce Freemen Rail Trail, Nara Park, Kimball’s farm in Westford and historical Concord just to name a few. Situated Thirty minutes west of Boston makes it easily accessible to all routes north, south, east and west.

Guest favourite
A charming two-story house features a blue exterior with white trim. A spacious front porch is adorned with white railings. Surrounding trees display colorful autumn foliage, and a paved driveway leads to the house, enhancing its welcoming appearance.
Home in Lowell
4.99 out of 5 average rating, 67 reviews

Home Away From Home in Lowell

This stylish and thoughtfully updated home is perfect for group getaways or family trips. Located just minutes from UMASS Lowell and other area attractions, it’s designed to feel like home—while you're away from home. Enjoy easy access to everything beautiful Lowell has to offer while staying in a fully private home with modern comforts, convenient amenities, and a charming outdoor space.

Top Guest favourite
A bright dining area features a wooden table surrounded by four chairs. Large windows frame views of the surrounding trees, allowing natural light to fill the space. A plant stand with greenery adds a touch of nature to the room.
Home in Groton
4.97 out of 5 average rating, 65 reviews

Balsam Retreat

What once was a small summer lake house has been transformed into a newly remodeled retreat. Charming and private with amenities like a woodstove and laundry, this cozy retreat is only blocks from a lake and minutes from downtown Groton. This is a two family home, but you have your own entrance, parking spaces, and back deck located between the two homes.

Popular amenities for Chelmsford holiday rentals

When is the best time to visit Chelmsford?

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Avg. price$115 NZD$115 NZD$115 NZD$112 NZD$115 NZD$119 NZD$124 NZD$115 NZD$115 NZD$115 NZD$115 NZD$106 NZD
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Quick stats about holiday rentals in Chelmsford

  • Total holiday rentals

    Explore 100 holiday rentals in Chelmsford

  • Nightly prices starting at

    Chelmsford holiday rentals start at $71 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,060 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Chelmsford holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chelmsford rentals

  • 4.7 Average rating

    Chelmsford stays receive an average rating of 4.7 out of 5 from guests