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Vacation rentals in Chelmsford

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Top-rated vacation rentals in Chelmsford

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite

4.99 out of 5 average rating, 260 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.

Guest suite

5 out of 5 average rating, 164 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Guest suite

4.97 out of 5 average rating, 253 reviews

Relaxing 2 Room Suite with Private Bath/Deck/Patio

Welcome to this spacious, quiet and relaxing furnished suite (private entrance own deck- patio-fire pit). It is truly in an amazing location; walking distance to Mall/Lahey Hospital & only 18 mi from Boston Logan Airport, with plenty of parking. Our place is good for professionals, students, couples, solo, families (with kids). The airbnb is attached to a main house but it's contactless (check-in/-out) with own entrance. Ideal for 2, a little tight for 3 but manageable (sofa into bed).

Rental unit

4.87 out of 5 average rating, 201 reviews

The Estate Escape with Hottub

The apartment is new with high-end finishes, but there is still a storage container outside in the front of the house. (See pictures.) Cozy up during your next trip to southern New Hampshire! The Estate Escape is a perfect place for a peaceful escape with its own hot tub. The Estate Escape is minutes away from Canobie Lake Park, Castleton, and La Belle Winery. It is a short drive to Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Guest suite

4.98 out of 5 average rating, 242 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Season now closed, see you in Spring! Not an 'entire' home but more than a room. On a lovely small lake with a panoramic view from the bedroom, a spa-like bathroom, cotton linens, and a comfy bed, A/C and a living room. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy mill history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants and tax-free shopping. 1 hr from Boston, central to New England.

Guest suite

4.99 out of 5 average rating, 192 reviews

Guest suite with king bed and private entrance

Come and relax in our spacious one-bedroom basement guest suite that is comfortable and bright. It has a private entrance with off street parking. The suite has a large living area, bedroom with king bed and private bath . The location is an ideal 20 minutes from the Manchester/Boston Regional airport and 10 minutes from the Merrimack Premium Outlets as well as a wide variety of restaurants. Boston, skiing, the beach and the #1 most hiked mountain in the world are all about an hour away.

Barn

4.88 out of 5 average rating, 410 reviews

✨Private Studio w/ Loft Center Historic Carlisle✨

ENTIRE PLACE. This is a private charming studio completely separate with no shared areas located in the center of beautiful Carlisle. Close proximity to Routes 128, 495 and 3. Just 25 mins from Cambridge, Somerville, Boston. A pleasant 10 min to historic downtown Concord's lively events, shops and restaurants. 1.6 miles to Hiking/bike trails of Great Brook Farm State Park. Explore nearby hiking, conservation land and farms. *Only a 15 min drive to Lowell via the Lowell Connector*

Guest suite

4.98 out of 5 average rating, 141 reviews

Peaceful, Private 1 Bedroom Apartment, & Porch

Quiet private 1 bedroom apartment with separate entry adjacent to the home. A private porch with an infrared grill offers relaxing outdoor space and ambiance. Great for couples, adventurers, and business travelers. A drive or short walk brings you to several restaurants and shopping stores. Downtown is a bicycling trail and commuter rail station from Ayer to Boston. Outdoor enthusiasts, rent kayaks at Nashua River or enjoy walks. Devens and Coed Boarding School in Groton is nearby.

Home

5 out of 5 average rating, 167 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 suite

4.97 out of 5 average rating, 115 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 suite

4.97 out of 5 average rating, 139 reviews

Pine Estate - Private suite

Welcome to our spacious guesthouse located - 2 miles from Nashua - 5 minutes drive to the highway - 40 minutes to Boston and minutes from Hollis. Hollis is an active farming community offering beautiful orchards, nature paths, art studios and a winery. Beautiful private yard with a large patio where you can relax and enjoy nature at its best. Our place is ideal for a weekend get-away or business travelers. Please note there will be no exception to the no pets policy.

Guest suite

4.91 out of 5 average rating, 367 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.

Vacation rentals for every style

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Hotels

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Unique stays

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Popular amenities for Chelmsford vacation rentals

Free parking on premises

Air conditioning

Stay near Chelmsford's top sights

University of Massachusetts Lowell4 locals recommend

Mill No. 515 locals recommend

Lowell National Historical Park13 locals recommend

Showcase Cinema de Lux Lowell11 locals recommend

Whole Foods Market10 locals recommend

1981 Ramen Bar9 locals recommend

Other great vacation rentals in Chelmsford

Home

5 out of 5 average rating, 16 reviews

* * Crooked_Spring_Colonial * *

Home

4.86 out of 5 average rating, 51 reviews

Entire Townhouse with Parking

Guest suite

4.97 out of 5 average rating, 91 reviews

Comfortable studio space in country setting Groton

Guest suite

4.99 out of 5 average rating, 86 reviews

Air "Bee-n-Bee"' Hive | Unique Themed Getaway

Townhouse

4.81 out of 5 average rating, 26 reviews

Entire Unit near UMASS Lowell

Guest suite

4.92 out of 5 average rating, 24 reviews

Waterfront retreat in Concord

Rental unit

4.92 out of 5 average rating, 26 reviews

Zen Garden in Lowell | 45mins to BOS MA

Home

4.89 out of 5 average rating, 35 reviews

Private studio apartment(in the basement)

Quick stats about vacation rentals in Chelmsford

Total rentals
100 properties
Nightly prices starting at
€ 19 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 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 North Chelmsford, and over 170 vacation rentals in South Lowell.
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 Apartment Rentals in Chelmsford?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, 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 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 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 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.

Destinations to explore