Holiday rentals in Chelmsford

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Top-rated holiday rentals in Chelmsford

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Guest favourite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 217 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!

5–12 Aug

$172 SGD per night

Guest favourite

Flat in Concord

4.95 out of 5 average rating, 164 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). Discounts for stays of longer than 2 weeks.$75 additional cleaning fee for stays over 2 weeks.

11–18 Mar

$199 SGD per night

Guest favourite

Guest suite in Windham

4.99 out of 5 average rating, 243 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.

12–19 Feb

$186 SGD per night

Guest favourite

Flat in Billerica

4.96 out of 5 average rating, 103 reviews

Unique Artist's Home->Sunporch Gallery, Cook, Read

~ Heated Stones Bathroom Floor --- Parking --- Laundry --- Wi-Fi --- Crib --- Coffee --- 35 min. drive to Boston --- 19 min. walk to Train Station ~ This is a quirky renovation of a nice old house. It is across the street from the Concord River. We're creating a tiny orchard as an experiment in sustainability as art. - family owned (25 yrs). - 2 stories, 840 sq ft. - kitchen + dining nook w/ restored tin ceiling. - double vanity copper sinks. - art books. - bonus: movie lounge w/ projector.

6–13 Feb

$247 SGD per night

Guest favourite

Cabin in Littleton

4.98 out of 5 average rating, 114 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

A bit of a wonderland (57 Acers, 50+ 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.

5–12 Jul

$242 SGD per night

Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 106 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

1–8 Jan

$173 SGD per night

Guest favourite

Guest suite in Merrimack

4.99 out of 5 average rating, 150 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.

25 Jul – 1 Aug

$127 SGD per night

Guest favourite

Barn in Carlisle

4.84 out of 5 average rating, 513 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*

18–25 Feb

$171 SGD per night

Guest favourite

Home in Chelmsford

5.0 out of 5 average rating, 118 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.

14–21 Apr

$497 SGD per night

Guest favourite

Guest suite in Hollis

4.98 out of 5 average rating, 114 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.

24–31 Jul

$158 SGD per night

Guest favourite

Guest suite in Littleton

4.91 out of 5 average rating, 315 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.

19–26 Sep

$146 SGD per night

Guest favourite

Flat in Andover

4.92 out of 5 average rating, 114 reviews

Villa Ricci

Come stay in our private, cozy garden level apartment in the lower level of our home in Andover MA. We are in a quiet neighborhood within walking distance to Andover Landing at Brickstone Square and a short ride to Philips Andover, downtown Andover, Merrimack College, and 16 miles to Boston. We are close to 93 and 495 for quick access to NH, ME and Boston. Enjoy your own driveway, outdoor space, and entrance. Come stay with us.

19–26 Nov

$172 SGD per night