Holiday rentals in Chelmsford

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Top-rated holiday rentals in Chelmsford

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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.
Flat in Billerica
4.99 out of 5 average rating, 164 reviews

Air Bee-n-Bee Hive: Coffee Bar, Fresh Eggs & Charm

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 stylish living area features a dark leather sofa positioned near a modern glass coffee table. A flat-screen television sits on a black media unit. Two windows provide natural light and a dining table is set for four, enhancing the open and functional layout.
Apartment in Centralville
4.86 out of 5 average rating, 121 reviews

Cozy Entire Unit Condo close to UMASS Lowell

My place is close to restaurants, UMASS. Lowell, and almost anything you need. You’ll love my place because instead of having a spare room in someone's house, you get an entire condo and privacy available to you (owner lives in separate unit). The unit includes basic amenities included (toiletries, bedding etc). In addition, the unit comes with a PlayStation 4 for the kids (or the husband/boyfriend) to keep them busy :) My place is good for couples, solo adventurers, and business travelers.

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.
Apartment in North Chelmsford
4.84 out of 5 average rating, 32 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

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.
Apartment in North Chelmsford
4.88 out of 5 average rating, 101 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.
Flat in Westford
4.94 out of 5 average rating, 117 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.
Flat 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, 227 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, 437 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.

Guest favourite
A spacious living area features a large, sectional couch arranged around a coffee table. Light-colored walls reflect the brightness from multiple recessed lights. In the background, a kitchenette with seating for eight is visible, creating an open and inviting space.
Guest suite in Tyngsborough
4.85 out of 5 average rating, 20 reviews

Althea’s Retreat

Located on the lower level of our home, you will find a spacious suite complete w/living room w/pullout couch, kitchenette w/lots of seating, mini fridge, microwave, dishwasher,2 TV’s,full bath, and a private bedroom with a full bed. Sliders access the private backyard overlooking the lake (fishing galore). We also have a pool table for your enjoyment. located near Nashua, NH home of “The Nash” casino, & Lowell, MA near UMass Lowell. 40 mins to Boston.

Top guest favourite
A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.
Guest suite in Lexington
4.97 out of 5 average rating, 147 reviews

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

Guest favourite
The exterior of a modern two-story house is highlighted, featuring large windows and a welcoming entrance with a wooden door. Solar panels are visible on the roof. Neatly trimmed bushes and a well-maintained lawn contribute to the home's inviting appearance.
Home in Pawtucketville
4.88 out of 5 average rating, 43 reviews

Private studio apartment(in the basement)

This elegant basement facility falls into the category of a self-contained suite nested inside our main house. It has a luxury king-size mattress that sleeps two. It also features a sofa bed, extra furnishings along with WIFI, and a smart TV for streaming. An attached full bathroom has all the required supplies. The kitchenette also has all the amenities. You will find a thoughtful manual with all the information you need.

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, 64 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

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 £30 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    100 of Chelmsford holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chelmsford rentals

  • 4.7 Average rating

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