Holiday rentals 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 living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.
Loft in Peterborough
5 out of 5 average rating, 234 reviews

Peaceful Mill with Waterfall - Home Away From Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Top guest favourite
The kitchen area showcases modern appliances including a black refrigerator and gas stove. A spacious countertop offers ample prep space. Light wood flooring complements the white cabinetry. Seating for four is available at the round table, illuminated by natural light from the adjacent windows.
Home in Bedford
4.92 out of 5 average rating, 168 reviews

Modern 2BR with A/C for your Business and Pleasure

Ideal location for business travelers or small families. Enjoy a comfortable experience at this centrally-located place. Don’t be fooled by the size of our 600SF home, it has everything you could need - fast WIFI, fully stocked kitchen, central AC, gas stove, insta hot water, fridge with ice & filtered water on the door, and a soaking tub. Conveniently located by Hanscom AFB, Hartwell Business Corridor, Wiggins Ave Technology District, MIT Lincoln Lab, Edge Sports Center & the Minuteman Bikeway.

Guest favourite
A modern kitchen is presented with white cabinets and stainless steel appliances, including a refrigerator and oven. Granite countertops provide ample workspace, with a sink beneath a window. Natural light fills the area, enhancing the open and inviting atmosphere.
Flat in Windham
4.88 out of 5 average rating, 354 reviews

The Cozy Corner Apartment

Cozy up during your next trip to the southern New Hampshire area! The Cozy Corner is a combination of style and comfort in so many ways from the double windows and sliding glass doors that flood the space with light to the airy and peaceful design that makes it feel like home. The Cozy Corner is a short drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston and NH Seacoast, close to Lakes Region, White mountains, and great skiing spots. 10 minutes from major shopping centers!

Top guest favourite
Flat in Woburn
4.95 out of 5 average rating, 220 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

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
4.87 out of 5 average rating, 108 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 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, 289 reviews

Winery Studio w/ Private Hot Tub & Wine Tasting

Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

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
4.95 out of 5 average rating, 134 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, 243 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
Home in Ipswich
4.9 out of 5 average rating, 118 reviews

Hillside Ocean View 2BR with Private Beach Access

Cozy, light-filled home just a 10-min walk to Pavilion Beach with access to private Clark Beach too. Open living space with ocean views, comfy seating, fast WiFi, and streaming. Enjoy sunrises from the queen bed in the main bedroom; second bedroom also has a queen. Fully equipped kitchen with lobster pot and dishwasher. Relax in the ocean-facing sunroom or grill on the balcony with stunning views. Perfect for families or small groups seeking a relaxing beach escape.

Top guest favourite
The living area is designed with British influence, featuring a blue sofa with Union Jack cushions and a white sofa. A round wooden coffee table is positioned at the center, surrounded by a colorful area rug. A ceiling fan and a large television complement the space.
Flat in North Andover
4.97 out of 5 average rating, 148 reviews

3 room suite, 24 miles to Boston, British decor

Lovely new 3 Room suite with Full kitchen. Ideal suburban location. 24 miles north of Boston, close to NH border. 25 min ride to NH beaches, Hampton and Rye. About 35 mins. to Salem, MA. Close to Merrimack College and Phillips Academy. You will feel at home in this spacious apt. Enjoy British influence decor. Perfect for couples or families. Unique Outdoor Pizza Oven experience can be arranged, weather permitting. Please inquire.

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
4.98 out of 5 average rating, 191 reviews

Bee-Themed Retreat Near Boston - Unique Stay

Experience a one-of-a-kind stay at the Bee Hive in Billerica, a delightful apartment uniquely themed around honeybees. Located just 21 miles from vibrant Boston, enjoy close proximity to city attractions while relaxing in a charming, peaceful garden setting. Perfect for couples, families, or remote workers seeking inspiration and tranquility.

Top guest favourite
A detached studio guesthouse is depicted, featuring a clean, neutral-toned exterior with a welcoming front door. Surrounding greenery includes shrubs and neatly arranged stones. A small wooden well is visible, adding charm to the peaceful outdoor setting.
Guest house in Westford
4.97 out of 5 average rating, 122 reviews

Detached Waterfront Guest House

Fully furnished and equipped rental in MA. This completely renovated detached private studio guesthouse is ideal with peaceful setting and your own private outdoor deck overlooking the pond. Located in the beautiful town of Westford MA. Just 35 to 40 min northwest of Boston and 10 minutes from the NH border. Five minutes to US Route 3.

Popular amenities for Chelmsford holiday rentals

When is the best time to visit Chelmsford?

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Frequently Asked Questions

  • 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.

  • 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.

  • 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.

  • Where should I stay in Chelmsford?

    Make yourself at home in Chelmsford by choosing from our most frequently booked neighborhoods. We have over 150 vacation rentals in Pawtucketville, over 100 vacation rentals in Heart Pond, and over 180 vacation rentals in North Chelmsford.

  • Do hotel rentals in Chelmsford have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning 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 wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Chelmsford. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chelmsford have free parking?

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

  • What are the most popular amenities for Bed And Breakfast Rentals in Chelmsford?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 £30 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 & 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

    110 of Chelmsford holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chelmsford rentals

  • 4.8 Average rating

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