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Holiday houses in Chelmsford

Find and book unique accommodation on Airbnb

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, 301 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
A comfortable living room is showcased with a blue sofa and two light-colored armchairs. A coffee table sits in the center, adorned with decorative items. Warm wood flooring complements the subtle hues of the walls, while soft lighting enhances the welcoming atmosphere.
Apartment in Woburn
5 out of 5 average rating, 179 reviews

Charming 1 BR private entrance apt commuters dream

Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

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, 106 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 favourite
The dining area features a wooden table surrounded by four high-backed chairs. A large piece of artwork is displayed on the wall, and a potted plant adds a touch of greenery. The open kitchen is visible in the background, equipped with modern appliances.
Apartment in Derry
4.85 out of 5 average rating, 105 reviews

3 Bedroom Apartment in Downtown Derry

Cozy up during your next trip to southern NH! Built in 1910, this apartment has been completely renovated. Meadowview is a combination of elegance and comfort from the walls of windows that flood the space with light and scenic conservation/golf course views to the spacious backyard that is perfect for a peaceful escape. It is 5 minutes from i-93 and a short drive to Canobie Lake Park, Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Guest favourite
Apartment in Strawberry Hill
4.94 out of 5 average rating, 563 reviews

Spacious Strawberry Hill Suite (West Cambridge)

This 3rd floor suite is less than 2 miles west of Harvard Sq. You'll have exclusive access to the space, which has a full bathroom and kitchenette. There is a queen bed suitable for two people and the couch in the living room converts to a bed for one. Our neighborhood is friendly, safe, and has a lot to offer. Public transportation (bus) is a 5 minute walk. The trip to Harvard Square is 10-15 minutes. I live in the home downstairs and am available should you need me during your stay.

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
4.95 out of 5 average rating, 131 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 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, 236 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 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, 281 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 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, 143 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)

Top Guest favourite
A bedside table with a wooden surface and black drawer is positioned next to a spacious bed. A lamp with a white shade and a black base features golden accents, providing a soft glow in the room. Neutral-colored bedding adds to the calming atmosphere.
Apartment in Woburn
4.97 out of 5 average rating, 104 reviews

Newly Built En Suite

Accommodations by Veteran Airbnb Hosts, we present An En suite in a new construction townhome. On the fringe of the suburbs, This special place is close to everything, making it easy to plan your visit. You have your own Entrance/exit into your space. 12 1/2 foot High cielings in your dedicated Level of the building gives this space a very West Coast feel. Walk out to your own Private patio for dining or relaxing as well as some shared greenspace to walk your fury friend.

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, 451 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 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, 158 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

Popular amenities for Chelmsford holiday rentals

When is the best time to visit Chelmsford?

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Avg. price$108 NZD$108 NZD$108 NZD$104 NZD$108 NZD$111 NZD$116 NZD$108 NZD$108 NZD$111 NZD$114 NZD$113 NZD
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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 180 vacation rentals in North Chelmsford, over 100 vacation rentals in Heart Pond, and over 150 vacation rentals in Pawtucketville.

  • Do apartment rentals in Chelmsford have free parking?

    Absolutely! We offer over 10 apartment 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 wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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

    Experience the best of Chelmsford with our hotel rentals, starting at about $190 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 apartment rentals in Chelmsford have wifi?

    Absolutely! We offer over 10 apartment 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 apartment rentals in Chelmsford have air conditioning?

    Absolutely! We offer over 10 apartment 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 110 holiday rentals in Chelmsford

  • Nightly prices starting at

    Chelmsford holiday rentals start at $66 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,410 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

    110 of Chelmsford holiday rentals include Wi-Fi access

  • Popular amenities for guests

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

  • 4.8 Average rating

    Chelmsford stays are highly rated by guests—averaging 4.8 out of 5!