Discover house sitting in Head of Westport banner

Discover house sitting in Head of Westport

Stay in wonderful places by house sitting and caring for cute pets.

  1. Home
  2. House & Pet Sitting Assignments
  3. United States
  4. Massachusetts
  5. Head of Westport

143 house sits in Head of Westport, MA, US

Looking for pet sitters in Head of Westport?

House sit in North Dartmouth, MA, US
House sit pet parent - Come hang with Levon and work or relax in a coastal Massachusetts town!

Come hang with Levon and work or relax in a coastal Massachusetts town!

from 30 November 2026 to 05 December 2026 · 5 nights

North Dartmouth, MA, US

  • 1 dog
House sit in Fairhaven, MA, US
House sit pet parent - Historic Seaport Setting.

Historic Seaport Setting.

from 26 December 2026 to 03 January 2027 · 8 nights

Fairhaven, MA, US

  • 3 dogs
House sit in Wareham, MA, US
House sit pet parent - Cozy Home + Sweet Dogs

Cozy Home + Sweet Dogs

from 30 December 2026 to 06 January 2027 · 7 nights

Wareham, MA, US

  • 2 dogs
House sit in Attleboro, MA, US
House sit pet parent - Looking for someone to stay in our centrally located home , & baby our pets.

Looking for someone to stay in our centrally located home , & baby our pets.

from 14 December 2026 to 08 January 2027 · 25 nights

Attleboro, MA, US

  • 3 dogs
  • 1 cat
House sit in Attleboro, MA, US
House sit pet parent - Cozy cottage with a very cute cat in Attleboro, Massachusetts.

Cozy cottage with a very cute cat in Attleboro, Massachusetts.

from 02 December 2026 to 06 December 2026 · 4 nights

Attleboro, MA, US

  • 1 cat
House sit in East Falmouth, MA, US
House sit pet parent - Cape Cod coastal boho home with loving pets

Cape Cod coastal boho home with loving pets

from 11 December 2026 to 13 December 2026 · 2 nights

East Falmouth, MA, US

  • 3 or more pets
House sit in Oak Bluffs, MA, US
House sit pet parent - Have a great vacation on Martha's Vineyard with 2 adorable Sheltie brothers!

Have a great vacation on Martha's Vineyard with 2 adorable Sheltie brothers!

from 22 December 2026 to 29 December 2026 · 7 nights

Oak Bluffs, MA, US

  • 2 dogs
House sit in Mansfield, MA, US
New
House sit pet parent - Relaxing Stay Near Providence and Boston

Relaxing Stay Near Providence and Boston

from 14 November 2026 to 18 November 2026 · 4 nights

Mansfield, MA, US

  • 1 dog
  • 2 reptiles
House sit in Mashpee, MA, US
House sit pet parent - Enjoy our spacious and sunny home on Cape Cod with our loving dog & cat.

Enjoy our spacious and sunny home on Cape Cod with our loving dog & cat.

from 05 January 2027 to 12 January 2027 · 7 nights+ 1 more

Mashpee, MA, US

  • 1 dog
  • 1 cat
House sit in Mashpee, MA, US
Last minute
House sit pet parent - Cape Cod Home

Cape Cod Home

from 09 October 2026 to 11 October 2026 · 2 nights

Mashpee, MA, US

  • 4 dogs
House sit in Plymouth, MA, US
House sit pet parent - Historic Plymouth!

Historic Plymouth!

from 12 January 2027 to 23 January 2027 · 11 nights

Plymouth, MA, US

  • 1 dog
  • 3 cats
House sit in Plymouth, MA, US
House sit pet parent - Plymouth MA- close to the beach with a friendly and super mellow lab.

Plymouth MA- close to the beach with a friendly and super mellow lab.

from 27 February 2027 to 28 February 2027 · 1 night

Plymouth, MA, US

  • 1 dog
  2. 1
  3. 2
  4. 3

Why you'll love pet and house sitting in Head of Westport, MA

An illustration of a cat laying on his pet bedForget hotel rooms

From home comforts to the calming company of pets, house sitting offers so much more.

An illustration of a glowing green heartIt feels good to give

Explore new places while making a difference to the lives of pets and people along the way.

An illustration of a house with a tree in the foregroundA new perspective

You don’t have to travel far. With pet and house sitting, you can find a world of adventures just around the corner.

An illustration of three coins with paws in them

A win-win without money

On house and pet sits, you’ll provide home and pet care in return for a place to stay on your travels. An annual plan unlocks unlimited access to sits, making it an affordable and fulfilling way to travel.

Find out more about memberships
“

I am so blessed to have this experience and to be able to have a companion by my side the entire time. I’m forever grateful for the opportunity TrustedHousesitters provides! This is truly life changing.

Adelia, sitter member from Bath, UK

Popular pet sitting and house sitting destinations

Feel safe, secure and supported

An illustration of a speech balloon with five stars on itRead feedback from sitters

Want to know if a house sit is right for you? Look for feedback previous sitters have left on the pet parent's listing.

An illustration of stacked documentsHome & Contents Plan

House sit in homes with peace of mind they’re covered at no extra cost to you or the pet parent.

An illustration of a dog sniffing the air24/7 Vet Advice Line

With a free direct line to a dedicated team of veterinary nurses, you can quickly clear up any pet queries.

Learn more about trust and safety

Ready to start your Head of Westport house sitting adventure?

Join our worldwide community and start your membership today.

Discover pet and house sits across the United States

Nearby locations

Locations in United States

Cities Worldwide

Countries

Head of Westport house sitting FAQs

All that’s exchanged between our sitters and pet parents is trust - sitters get to stay in cool locations near and far, caring for pets with a place to stay in return. And with no money passing hands, we’re certain everybody’s here for the same reasons: their never-ending love for pets and travel.

With an annual sitter membership, animal lovers like you can explore the world and enjoy unique stays in exchange for pet care. Live like a local, care for adorable pets, and provide pet parents with peace of mind while they’re away. Apply for as many sits as you like and get ready for meaningful connections and unforgettable adventures.

Choose your membership plan and create a profile that stands out from the pack - include clear photos, relevant experience, and references (these don’t have to be from previous house sits). Next, set up a saved search to be the first to find out when house sitting opportunities in Head of Westport become available for your chosen dates. Once you’ve found the ideal sit, write a personalized message to the pet parents explaining why you're the perfect person for their furry friend! Find out more with 10 tips on how to become a house sitter.

Your number one priority when house sitting in Head of Westport will be taking care of the pets. Daily walks, mealtimes, and lots of cuddles will be top of the agenda as most house sits include a pet. Aside from this, house sitters in Head of Westport need to keep the home clean and tidy and send regular updates to the pet parents about their precious pet pals.

At TrustedHousesitters, our members are driven by a genuine love of pets, not money. They exchange loving pet care for a place to stay on their travels, gaining a wealth of experiences and memories to last a lifetime.

© 2026 TrustedHousesitters.com ™
Help keep your account up to date

Verify your email to stay connected with other members and receive important updates.