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
A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.
Guest suite in Windham
4.99 out of 5 average rating, 292 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

Top Guest favourite
Apartment in Billerica
4.99 out of 5 average rating, 169 reviews

Air Bee-n-Bee Hive– Unique Themed Creative Retreat

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, 34 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.
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, 122 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, 230 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.

Guest favourite
The exterior of the contemporary two-story apartment building is presented, featuring a blend of white and dark siding. Two balconies with railings are visible at the front, along with large windows that enhance natural light. A manicured pathway leads to the entrance.
Apartment in Centralville
4.94 out of 5 average rating, 99 reviews

Modern, All New 3BR Near UMASS

Welcome to our modern, fully renovated 3-bedroom apartment in Lowell! Just minutes from downtown, UMASS, top restaurants, cafes, and local attractions. Whether you're here for a weekend getaway, work trip, college visit, or extended stay, this space offers comfort and convenience. Enjoy a stocked kitchen, fast Wi-Fi, Smart TV, in-unit laundry, and a private balcony. Perfect for families, professionals, traveling nurses, and anyone looking for a clean, cozy place to call home.

Top Guest favourite
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, 137 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 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, 443 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.

Popular amenities for Chelmsford holiday rentals

When is the best time to visit Chelmsford?

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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 Hotel Rentals in Chelmsford?

    Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in bed and breakfast rentals in Chelmsford?

    Experience the best of Chelmsford with our bed and breakfast rentals, starting at about $50 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 30 vacation rentals for guests traveling with pets.

  • Do hotel rentals in Chelmsford have wifi?

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

  • Do bed and breakfast rentals in Chelmsford have a kitchen?

    Absolutely! We offer over 20 bed and breakfast 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.

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 $61 AUD 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