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
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, 316 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
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
4.93 out of 5 average rating, 175 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.

Top guest favourite
A quaint cabin is positioned among trees, softly lit at night. An illuminated entrance is framed by colorful pots and surrounded by a cozy seating area with an Adirondack chair. Flickering firelight adds warmth to the inviting outdoor space.
Cabin in Littleton
4.99 out of 5 average rating, 218 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Top guest favourite
Flat in Woburn
4.95 out of 5 average rating, 229 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, 112 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, 294 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
A serene lakeside view captures a vibrant sunset with the sun partially descending behind distant hills. A lone fisherman in a boat is visible on the water, while a wooden deck features seating arrangements surrounded by lush plants.
Guest suite in Tyngsborough
4.98 out of 5 average rating, 267 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

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, 249 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 exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Flat in Groton
5 out of 5 average rating, 100 reviews

Farmhouse Guest Apartment

Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, table & chairs you may use.

Top guest favourite
A contemporary cabin retreat is nestled among tall trees, softly illuminated by warm outdoor lights. A wooden deck with steps leads to a welcoming entrance. A separate sauna structure is visible, surrounded by snow-covered ground, providing a serene atmosphere in a tranquil forest setting.
Home in South Berwick
5 out of 5 average rating, 134 reviews

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Top guest favourite
A private entrance to a charming home is framed by well-maintained landscaping and a gravel driveway. Decorative flower boxes adorn the windows of the light-colored exterior, while surrounding trees provide a natural backdrop, creating a serene environment.
Flat in Concord
4.96 out of 5 average rating, 227 reviews

Mema's Place --Lovely apartment in private home

This private apartment in a lovely home in historic Concord, Massachusetts features one bedroom with queen bed, living room, kitchen, bathroom, and porch. Your apartment is locked off from the rest of the home and you have your own entrance. We are within 4 miles of Concord Academy, Middlesex School, the North Bridge, Sleepy Hollow Cemetery (where Alcott, Thoreau, Emerson, and Hawthorne are buried).

Top guest favourite
Home in Nashua
4.93 out of 5 average rating, 312 reviews

Nashua Victorian

Two family Victorian in very quiet neighborhood. 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, 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.

Popular amenities for Chelmsford holiday rentals

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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 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 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 house rentals in Chelmsford have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning 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 bed and breakfast rentals in Chelmsford have wifi?

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

  • Do bed and breakfast rentals in Chelmsford have free parking?

    Absolutely! We offer over 20 bed and breakfast rentals with free parking in Chelmsford. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with a kitchen, over 20 homes with air conditioning, over 10 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 3,600 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

  • 4.7 Average rating

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