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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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Home

5 out of 5 average rating, 43 reviews

New South End Home Quiet Lane To Old Garden Beach

Newer furnished home, 1/2 mile walk to quaint Bearskin Neck with Rockport shops & galleries. Old Garden Beach 1/4 mile walk down a quiet unpaved lane. 3 BR/3 Bath home available for summer weekly vacations. Family friendly, 3 prkg spaces, 2 decks, new appliances (laundry, microwave & dishwasher), hardwood floors, new rugs & beds, full basement w/ pool table, fenced yard. Several beaches, hiking trails nearby or take a train to Salem, Newburyport, or Boston. Longer term winter rental available

Apartment

4.96 out of 5 average rating, 301 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Apartment

4.89 out of 5 average rating, 101 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Apartment

4.88 out of 5 average rating, 126 reviews

View of Marsh & Dunes| Pet Friendly| Wkly Discount

***WINTER RENTAL AVAILABLE*** Inquire about winter rental rates for stays 2 months + Welcome to this truly unique property situated on one of the largest lots in all of PIum Island making it the perfect spot for outdoor entertaining! Enjoy the seclusion of this spectacular, scenic lot while being conveniently located just a short half block walk from the Sunset Club, Plum Island Grill, Beachcomba and The Cottage Creamery and also just a 7 minute walk to the beautiful Plum Island Beach!

Cottage

4.84 out of 5 average rating, 111 reviews

Sunset Bliss Beach 3 min + wood burning fireplace

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk to Plum Island Grill and the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

Guest suite

4.95 out of 5 average rating, 272 reviews

Romantic Spa By The Ocean. Hot Tub, Dining & Views

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

Home

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Home

5 out of 5 average rating, 18 reviews

Coastal Retreat

Welcome to our coastal rental, a charming retreat nestled in the heart of a vibrant beach town. With modern amenities and coastal decor, unwind in the light-filled spaces and savor beautiful marsh views from the well manicured backyard. Located about a mile from Main Street, you can walk or bike on the flat sidewalk to restaurants, shops and the harbor. Close by you'll also find a dog park, the beautiful public golf course, Widow's Walk and of course the beach!

Cottage

4.93 out of 5 average rating, 108 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Home

4.82 out of 5 average rating, 57 reviews

Sand Hills Beach - lighthouse area -

Walking distance to sand hills beach - One mile from center of town with restaurants and shops. Nearby basketball court. Very Close to Barker Tavern. Grassy backyard . New furnishings new full bath and new mattresses. bedrooms are upstairs. There is only one full bath upstairs Totally redone 2024. Bungalow beach style home. some guests find stairs to be “ steep” … my 82 year old mom does fine with the stairs and rail!

Home

4.8 out of 5 average rating, 183 reviews

Steps to Beach | Fireplace | Pat's Porch

Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.

Home

5 out of 5 average rating, 22 reviews

Hoyts Ahoy

Escape to the coastal beauty of Ogunquit, Maine, where your ideal vacation home awaits. This charming ranch-style 3-bedroom, 1.5-bathroom home has an appealing terrace and yard for gatherings, as well as a side patio with river and ocean views. The comfort and convenience are within steps of downtown Ogunquit, which offers everything from the beach, river, the famed Marginal Way, restaurants, and shops.

Vacation rentals for every style

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Apartments

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Houses

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Hotels

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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

4.93 out of 5 average rating, 125 reviews

Wachusett Mountain Get-Away

Home

4.92 out of 5 average rating, 13 reviews

Sunrise Beach Escape

Condo

4.94 out of 5 average rating, 108 reviews

Magical

Apartment

4.88 out of 5 average rating, 17 reviews

The Curie

Cottage

4.99 out of 5 average rating, 165 reviews

Plum Island’s TRUE NORTH COTTAGE

Home

4.9 out of 5 average rating, 127 reviews

NEW 3BR home, incredible views - Beach across St

Home

4.93 out of 5 average rating, 187 reviews

Charming New England Farmhouse

Cottage

4.83 out of 5 average rating, 18 reviews

Large Beach Cottage on York Beach, Maine

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 170 vacation rentals in North Chelmsford, over 90 vacation rentals in Heart Pond, 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 Hotel Rentals in Chelmsford?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, 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 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 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 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.

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