Vacation rentals in Chelmsford

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Top-rated vacation rentals in Chelmsford

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Guest favorite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 215 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Guests can enjoy our home's private suite on a lovely small lake with a panoramic view, a spa-like bathroom, cotton linens, and a comfy bed. A/C and a fireplaced living room. Quietly watch lake nature or boats going by, or venture out to swim, kayak, or fish. Enjoy Lowell's mill history and it's national park, take a forest walk nearby, or drive 10 min. to Nashua, NH for its many restaurants and tax-free shopping. 1 hr from Boston and central to New England highlights. Low cleaning fees!

May 29 – Jun 5

$109 per night

Guest favorite

Guest suite in Windham

4.99 out of 5 average rating, 242 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.

Jul 8 – 15

$137 per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 101 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

Jan 31 – Feb 7

$88 per night

Guest favorite

Home in Windham

4.92 out of 5 average rating, 258 reviews

One Level 2 bedroom suite on private cul-de-sac

Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

Jan 25 – Feb 1

$126 per night

Guest favorite

Guest suite in Merrimack

4.99 out of 5 average rating, 148 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.

Jun 12 – 19

$80 per night

Superhost

Barn in Carlisle

4.84 out of 5 average rating, 511 reviews

✨Entire Secluded Barn Suite Ctr 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*

Dec 29 – Jan 5

$108 per night

Guest favorite

Home in Chelmsford

5.0 out of 5 average rating, 117 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.

Dec 11 – 18

$311 per night

Guest favorite

Townhouse in Concord

4.93 out of 5 average rating, 329 reviews

Cottage Suite-Walk to Shops, Train. Town approved.

This is a private unit with no shared areas. It is the front corner of our house and is completely separate. However, you will share walls like in an apartment. Kitchen includes: sink, microwave, fridge, Keurig, and water boiler. Private gated outside lawn and patio. History, nature, dining & shopping are VERY CLOSE. Open and welcoming to ALL types of people. There is a CLEANING FEE in addition to the nightly fee. TV with internet (Prime, Hulu & Netflix) but NO LIVE TV OR CABLE

Jun 22 – 29

$162 per night

Guest favorite

Guest suite in Hollis

4.98 out of 5 average rating, 112 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.

Nov 20 – 27

$100 per night

Guest favorite

Guest suite in Littleton

4.91 out of 5 average rating, 312 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.

May 27 – Jun 3

$92 per night

Guest favorite

Apartment in Concord

4.94 out of 5 average rating, 207 reviews

Bishop Suite - Private suite in historic Concord

I live in historic Concord, Massachusetts, 4 miles from Concord Academy, Fenn School, Middlesex School, and many historical sites, and less than 30 miles from downtown Boston. About 4 miles from the commuter rail (train) to downtown Boston, and 2 miles to restaurants, grocery, and any kind of store you would need. For guests staying over 2 weeks, discounts can be negotiated, and an additional $75 cleaning fee will be assessed.

Feb 3 – 10

$99 per night

Guest favorite

Apartment in Lowell

4.96 out of 5 average rating, 130 reviews

Private Master & Living Room! Entire Space!

Looking for a quiet place to stay while in historic Lowell? Well, this is the place for you! Centrally located in a quiet neighborhood - 1/4 of a mile to UMass Lowell & 1 mile to downtown! You get a private master bedroom, bath, living room with pull out a sofa, NO kitchen, and 1 tandem driveway space. 30 miles to Boston & Airport, 2 miles to the commuter rail into Boston.

Jun 14 – 21

$95 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chelmsford vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chelmsford's top sights

Lowell National Historical Park13 locals recommend

Market Basket4 locals recommend

Lowell Memorial Auditorium7 locals recommend

Target3 locals recommend

Tsongas Center at UMass Lowell4 locals recommend

Showcase Cinema de Lux Lowell11 locals recommend

Other great vacation rentals in Chelmsford

Guest favorite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Jul 21 – 28

$102 per night

Guest favorite

Apartment in Andover

4.92 out of 5 average rating, 113 reviews

Villa Ricci

Aug 27 – Sep 3

$120 per night

Guest favorite

Guesthouse in Framingham

4.97 out of 5 average rating, 197 reviews

Private guest house on beautiful country road

Nov 9 – 16

$96 per night

Guest favorite

Guest suite in Burlington

4.98 out of 5 average rating, 202 reviews

Relaxing 2 Room Suite with Private Bath/Deck/Patio

Nov 11 – 18

$85 per night

Guest favorite

Apartment in Hudson

4.85 out of 5 average rating, 292 reviews

Private Mother-In-Law apartment on the lake!

Oct 4 – 11

$77 per night

Guest favorite

Guesthouse in Westford

4.97 out of 5 average rating, 79 reviews

Detached Waterfront Guest House

Nov 5 – 12

$94 per night

Guest favorite

Apartment in Westford

4.92 out of 5 average rating, 24 reviews

Furnished Cozy Apartment in quiet neighborhood

May 22 – 29

$68 per night

Guest favorite

Condo in Chelmsford

4.85 out of 5 average rating, 59 reviews

The Art Experience

Jan 15 – 22

$142 per night

Show all

Quick stats about vacation rentals in Chelmsford

Total rentals	90 properties
Rentals with dedicated workspaces	70 properties have a dedicated workspace
Pet-friendly rentals	20 properties allow pets
Family-friendly rentals	20 properties are a good fit for families
Total number of reviews	2K reviews
Nightly prices starting at	$20 before taxes and fees

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 80 vacation rentals in Heart Pond, over 130 vacation rentals in North Chelmsford, and over 140 vacation rentals in South Lowell.
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 $390 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 house rentals in Chelmsford have air conditioning?
Absolutely! We offer over 20 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 70 vacation rentals in Chelmsford featuring dedicated workspaces. Stay connected and productive in your home away from home.

Vacation rentals in Chelmsford

Top-rated vacation rentals in Chelmsford

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Chelmsford vacation rentals

Stay near Chelmsford's top sights

Other great vacation rentals in Chelmsford

Guest suite in Peabody

Apartment in Andover

Guesthouse in Framingham

Guest suite in Burlington

Apartment in Hudson

Guesthouse in Westford

Apartment in Westford

Condo in Chelmsford

Quick stats about vacation rentals in Chelmsford

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Chelmsford?

Do apartment rentals in Chelmsford have free parking?

What are the most popular amenities for Hotel Rentals in Chelmsford?

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

Are there pet-friendly vacation rentals in Chelmsford?

Do apartment rentals in Chelmsford have wifi?

Do apartment rentals in Chelmsford have a kitchen?

Do house rentals in Chelmsford have air conditioning?

Are there family-friendly vacation rentals in Chelmsford?

Are there vacation rentals with a dedicated workspace in Chelmsford?

Destinations to explore