Holiday Benefits - Vacation Rentals in Chelmsford

King size bed with continental breakfast. From US $61
         

10.0 (6 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Studio - Cozy Downtown Hideaway From US $138
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Guest Services
Travelway Inn Sudbury From US $130
         

8.8 (960 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Cozy Bancroft Stay in the Minnow Lake area From US $190
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
TNT Executive Suites 2 From US $208
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Waterfront Guest Suite From US $143
         

9.8 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
TNT Executive Suites 1 From US $197
         

9.6 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Quiet & Charming Home - Perfect for Extended Stays From US $211
         

Luxury Places to Stay in Chelmsford

Over 147+ Luxury Places to Stay in or Near Chelmsford
Jason Gary From US $834
         

New
Hotel
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Days Inn by Wyndham Sudbury & Conference Centre From US $489
         

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7.6 (1480 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub Delight, King Beds & Unforgettable Moments From US $299
         

9.2 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Econo Lodge From US $290
         

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7.1 (90 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Lake Nepahwin | Dock+Deck & A/C | Walk Everywhere From US $264
         

New
Apartment
  • Air Conditioner
  • Security/Safety
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Top-Rated Vacation Rentals with a Pool in Chelmsford

Over 13+ Top-Rated Vacation Rentals with a Pool in or Near Chelmsford
Microtel Inn & Suites by Wyndham Sudbury From US $129
         

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8.6 (1223 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Sudbury by IHG From US $129
         

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8.4 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Clarion Hotel From US $114
         

7.8 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Holiday Inn Sudbury by IHG From US $149
         

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7.4 (341 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Radisson Hotel Sudbury From US $120
         

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7.1 (1817 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Travelodge Hotel by Wyndham Sudbury From US $91
         

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7.1 (903 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Clarion Hotel From US $84
         

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7.0 (529 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Chelmsford

Over 45+ Pet-Friendly Vacation Rentals in or Near Chelmsford
Modern 3br 3 ba house near downtown w/amenities From US $244
         

9.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy Upper 1-BDRM Downtown Smart & Stylish From US $143
         

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9.0 (2 Reviews)
Apartment
  • Pet Friendly
  • Security/Safety
  • Fireplace/Heating
Comfy Flat | Hot Tub + Games From US $189
         

3.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Cozy Comfy Studio From US $79
         

8.6 (9 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
Charming 5br New Sudbury home w/AC, Cable + Wifi From US $252
         

7.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Island cottage Sudbury on Whitson Lake From US $144
         

10.0 (1 Review)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Chelmsford

Over 10+ Large Vacation Homes & Villas in or Near Chelmsford
Residence & Conference Centre - Sudbury North From US $74
         

7.1 (73 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Large & Private Luxury Executive Waterfront Lakeview Estate From US $521
         

9.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Comfy Flat | Hot Tub + Games From US $239
         

4.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly renovated 3 bedrooms and 1 bathrooms. Located in the prime location. From US $377
         

The Gym Retreat by Casa Cruze From US $205
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • Pool
  • Security/Safety
Fairbank Views & Lakeside Dining From US $500
         

New
Cottage
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Wheelchair Accessible Vacation Homes in Chelmsford

Over 6+ Wheelchair Accessible Vacation Homes in or Near Chelmsford
Renovated House Near Everything with Nature Trails From US $122
         

8.0 (1 Review)
House
  • Parking
  • TV
  • Wheelchair Accessible
Travelway Inn Sudbury From US $128
         

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8.3 (563 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Village Inn & Suites From US $90
         

7.8 (140 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Valley Inn Motel From US $83
         

8.2 (300 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Residence & Conference Centre - Sudbury West From US $62
         

7.6 (214 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Super 8 by Wyndham Sudbury ON From US $81
         

6.4 (359 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Chelmsford Vacation Rentals and Airbnb Places to Stay Under $200

Over 98+ Chelmsford Vacation Rentals and Airbnb Places to Stay Under $200
Cozy & Private Full Floor at Minnow Lake From US $66
         

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8.5 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Valley Inn Motel & Suites From US $100
         

8.6 (401 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Feel at home when you're away - in our Elgin Suite! From US $125
         

9.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
professionals, students or travellers shortstays! From US $80
         

2.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Smart & Affordable Stay, Opp. YMCA For Work/Travel From US $131
         

Instantly Bookable Vacation Homes in Chelmsford

Over 30+ Instantly Bookable Vacation Homes in or Near Chelmsford
Mama T's Oasis From US $215
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV
Your ideal Home Away From Home From US $109
         

10.0 (38 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Cozy 1 bedroom in the heart of Chelmsford! From US $76
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Two bedroom guest suite on the lake From US $233
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 3-Bedroom Home with 2 Full-Size Bathrooms From US $190
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Apt#3: Charming 2-bedrm at the Royale on Cedar with WiFi. 13%hst & 6%MAT incl. From US $77
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Cozy place away from home From US $190
         

9.6 (22 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Bedding/Linens

About Chelmsford Vacation Rentals

With more than 156 Chelmsford vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidaybenefits and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chelmsford.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidaybenefits Chelmsford, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chelmsford. Places to stay near Chelmsford are 347.51 ft² on average, with prices averaging US $155 a night.

Holidaybenefits makes it easy and safe to find and compare vacation rentals in Chelmsford with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chelmsford

Type Count
Holiday Apartments 71
Vacation Homes 46
Hotels 32
Cabin Rentals 3
B&B 2
Cottages 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Chelmsford

Pro Tip: Holidaybenefits makes it easy to compare the best listings on Holidaybenefits homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidaybenefits homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chelmsford.

Weather in Chelmsford

View the weather forecast for Chelmsford before booking your Chelmsford Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Chelmsford Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chelmsford?
How many vacation rentals have private pools in Chelmsford?

There are 1 vacation rentals with private pools near Chelmsford. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Chelmsford?

Currently, the total number of properties listed in 2026 is over 156 in the Chelmsford area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chelmsford.