Vacation rentals in Chelmsford

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Top-rated vacation rentals in Chelmsford

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Top guest favorite
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, 163 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 favorite
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.
Condo in Centralville
4.86 out of 5 average rating, 120 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.

Superhost
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
4.84 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 favorite
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, 100 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.

Guest favorite
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, 115 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.

Top guest favorite
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, 20 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 favorite
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.

Superhost
The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.
Farm stay in North Andover
4.95 out of 5 average rating, 271 reviews

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

Top guest favorite
A tranquil kettle pond is depicted, reflecting the surrounding wooded landscape and soft hues of the sky. The calm water creates a mirrored surface, enhancing the serene atmosphere of the natural setting.
Guest suite in Concord
4.98 out of 5 average rating, 135 reviews

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Guest favorite
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, 434 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 favorite
A scenic view of a river reflects autumn foliage along the banks. A fountain can be seen in the foreground, while a historic building with a steeple and nearby bridges are positioned in the background. The vibrant colors of the trees enhance the picturesque landscape.
Home in Nashua
4.92 out of 5 average rating, 292 reviews

Nashua Victorian

Two family Victorian in very quiet neighborhood. Just off of Main St, walking distance to grocery store, fast food, drug stores and sit down restaurants. 1/2 mile to Rivier University. Parking for 3 cars. Private entrance. Can engage with owners (next door) or not, your choice. Complimentary Wifi . Home was built in the 1930's, beautiful woodwork and hard wood floors, yet updated with modern amenities. There is a $10/guest per night fee for each guest over 4.

Top guest favorite
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, 63 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 vacation rentals

Quick stats about vacation rentals in Chelmsford

  • Total rentals

    100 properties

  • Nightly prices starting at

    € 34 before taxes and fees

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Chelmsford?

    Make yourself at home in Chelmsford by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Heart Pond, over 170 vacation rentals in South Lowell, and over 180 vacation rentals in North Chelmsford.

  • Do house rentals in Chelmsford have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Chelmsford. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Chelmsford?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with free parking, over 40 homes with wifi, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in house rentals in Chelmsford?

    Experience the best of Chelmsford with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Chelmsford?

    Four-legged friends are welcome in Chelmsford. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do house rentals in Chelmsford have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Chelmsford. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Chelmsford have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Chelmsford. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chelmsford have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Chelmsford. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chelmsford?

    Chelmsford has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Chelmsford?

    Yes! Work meets play with ease at over 80 vacation rentals in Chelmsford featuring dedicated workspaces. Stay connected and productive in your home away from home.