Southeast Massachusetts Holiday Rentals

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Our top choices for Southeast Massachusetts holiday rentals

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (354 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
The price is AU$413
includes taxes & fees
28 Apr - 29 Apr
The Club at New Seabury

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (35 reviews)
"I had stayed here last year and it's so close to several of my family members. This is my go to place when I travel to the New Bedford area."
United States
Judy C.
The price is AU$312
includes taxes & fees
7 May - 8 May
The Charming Gem Near The Water!

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is AU$508
includes taxes & fees
8 May - 9 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,165 reviews)
"Staff was nice, very clean and quaint"
United States
John
The price is AU$143
includes taxes & fees
30 Apr - 1 May
Sandcastle Resort and Club

Sintra*romantic*near beach*private outdoor shower

Sintra*romantic*near beach*private outdoor shower
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"The owners are fantastic ! What a great property ! Beautiful place to stay, great location, easy access to beach . Couldn’t be happier!"
United States
Melissa M.
The price is AU$430
includes taxes & fees
26 Apr - 27 Apr
Sintra*romantic*near beach*private outdoor shower

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (52 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is AU$254
includes taxes & fees
27 Apr - 28 Apr
The Nantucket Room Unit - #2

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "
United States
ralpjh c.
The price is AU$612
includes taxes & fees
5 May - 6 May
Charming cottage overlooking the bay in Padanaram Village.

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (131 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is AU$528
includes taxes & fees
30 Apr - 1 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Park View ROOM @ Compound *E-Bike-Hot Tub -Boats

Park View ROOM @ Compound *E-Bike-Hot Tub -Boats
Cape Cod
The price is AU$345
includes taxes & fees
3 May - 4 May
Park View ROOM @ Compound *E-Bike-Hot Tub -Boats

Charming garden level 1 bedroom 1 bath apartment in Brockton

Charming garden level 1 bedroom 1 bath apartment in Brockton
Brockton
8.0 out of 10, Very good, (10 reviews)
"The apartment was clean and comfortable."
United States
Richard G.
The price is AU$231
includes taxes & fees
25 May - 26 May
Charming garden level 1 bedroom 1 bath apartment in Brockton

Tahiti*sleeps 5*near beach*fire pit*outdoor shower*grill

Tahiti*sleeps 5*near beach*fire pit*outdoor shower*grill
Plymouth
10.0 out of 10, Exceptional, (11 reviews)
"Our stay was great. The property was exactly as described and exceeded our expectations. Johanna was a great host and the cottage was well equipped for our needs. We look forward to staying again."
United States
Patrick R.
The price is AU$474
includes taxes & fees
26 Apr - 27 Apr
Tahiti*sleeps 5*near beach*fire pit*outdoor shower*grill

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen
Bayside
9.8 out of 10, Exceptional, (15 reviews)
"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "
United States
Candice C.
The price is AU$575
includes taxes & fees
26 Apr - 27 Apr
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is AU$966
includes taxes & fees
14 May - 15 May
6 Mi to Beach: Home w/ Deck in Brewster!

Quaint & Clean Cape Cod Loft

Quaint & Clean Cape Cod Loft
Bourne
10.0 out of 10, Exceptional, (18 reviews)
"Great location! Cute, quiet, neighborhood and so close to the beach. Perfect for our girls mini get away. "
United States
Jessica T.
The price is AU$436
includes taxes & fees
7 May - 8 May
Quaint & Clean Cape Cod Loft

Charming 2-bedroom building in delightful Hull with ocean view

Charming 2-bedroom building in delightful Hull with ocean view
Nantasket Beach
9.6 out of 10, Exceptional, (5 reviews)
"Stayed with family for a wedding reception close by. Location is outstanding. Walkable to all the beach restaurants and beach. "
United States
Sarah S.
The price is AU$494
includes taxes & fees
26 Apr - 27 Apr
Charming 2-bedroom building in delightful Hull with ocean view

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (102 reviews)
"We absolutely loved this house, very comfortable, well decorated and welcoming atmosphere. It was exactly what we needed for a weekend getaway. We will be back!"
United States
Margot C.
The price is AU$661
includes taxes & fees
27 Apr - 28 Apr
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

Santorini*themed*priv. yard*near beach* firepit*outdoor shwr
Plymouth
10.0 out of 10, Exceptional, (18 reviews)
"Very nice place. I’d stay there again!"
United States
Jamie C.
The price is AU$566
includes taxes & fees
26 Apr - 27 Apr
Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.8 out of 10, Exceptional, (18 reviews)
"Beds were comfortable, location was convenient for our needs, thankful for the shoveling and clearing of snow in the morning! "
United States
Stephanie G.
The price is AU$286
includes taxes & fees
26 Apr - 27 Apr
Charming 2-bedroom apartment with WiFi, AC in superb Canton

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is AU$336
includes taxes & fees
26 Apr - 27 Apr
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

383-Spacious NEW townhouse 7 beds 3 baths 20’To Boston

383-Spacious NEW townhouse 7 beds 3 baths 20’To Boston
Quincy
9.8 out of 10, Exceptional, (48 reviews)
"very clean. comfortable beds. Very nice stay."
Germany
Stefanie K.
The price is AU$466
includes taxes & fees
26 Apr - 27 Apr
383-Spacious NEW townhouse 7 beds 3 baths 20’To Boston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southeast Massachusetts Hotel Reviews

Find out more about Southeast Massachusetts

Everything you need to know about Southeast Massachusetts holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southeast Massachusetts holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southeast Massachusetts holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southeast Massachusetts holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southeast Massachusetts. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southeast Massachusetts holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southeast Massachusetts holiday rentals we have selected for you start as low as AU$143 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southeast Massachusetts rentals

At Expedia, we put the best Southeast Massachusetts holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southeast Massachusetts rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southeast Massachusetts holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southeast Massachusetts. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.