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, (355 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 NZ$444
includes taxes & fees
11 May - 12 May
The Club at New Seabury

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 NZ$609
includes taxes & fees
14 May - 15 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (37 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 NZ$370
includes taxes & fees
11 May - 12 May
The Charming Gem Near The Water!

Sandcastle Resort and Club

Sandcastle Resort and Club
3.0 star property
Provincetown
7.4 out of 10, Good, (1,169 reviews)
"love coming here ,outstanding staff, a lot of amenities, you can't go wrong choosing Sandcastle, can't wait to come back."
United States
Edward
The price is NZ$205
includes taxes & fees
12 May - 13 May
Sandcastle Resort and Club

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (263 reviews)
"Clean rooms and pool. Great family resort."
United States
Julie
The price is NZ$267
includes taxes & fees
12 May - 13 May
The Cove at Yarmouth by Westgate Resorts

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, (132 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 NZ$629
includes taxes & fees
11 May - 12 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Cozy Riverfront Stay in Wareham

Cozy Riverfront Stay in Wareham
Wareham
10.0 out of 10, Exceptional, (3 reviews)
"Perfect for wedding guests. Spacious, clean and great viewWould definitely stay again"
United States
Karleen L.
The price is NZ$731
includes taxes & fees
13 May - 14 May
Cozy Riverfront Stay in Wareham

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 NZ$499
includes taxes & fees
11 May - 12 May
Sintra*romantic*near beach*private outdoor shower

Charming Antique Boathouse Located Directly On Long Pond.

Charming Antique Boathouse Located Directly On Long Pond.
Plymouth
9.8 out of 10, Exceptional, (112 reviews)
"The hosts were very accommodating. Our arrival was late, and it was easy to get into the boathouse."
United States
Mark P.
The price is NZ$607
includes taxes & fees
3 June - 4 June
Charming Antique Boathouse Located Directly On Long Pond.

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 NZ$737
includes taxes & fees
13 May - 14 May
Charming cottage overlooking the bay in Padanaram Village.

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 NZ$289
includes taxes & fees
21 May - 22 May
Charming garden level 1 bedroom 1 bath apartment in Brockton

Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield

Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield
Marshfield
10.0 out of 10, Exceptional, (11 reviews)
"Great location and cozy cottage, would book again!"
United States
Erik N.
The price is NZ$661
includes taxes & fees
11 May - 12 May
Cozy cottage steps to beach sleeps 5 with WiFi, AC in charming Marshfield

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 NZ$676
includes taxes & fees
11 May - 12 May
Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA
Duxbury
10.0 out of 10, Exceptional, (33 reviews)
"Great location and wonderful property."
United States
brent w.
The price is NZ$700
includes taxes & fees
16 May - 17 May
Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (53 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is NZ$348
includes taxes & fees
11 May - 12 May
The Nantucket Room Unit - #2

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (111 reviews)
"Cute space and perfect size for me and my small dog!"
United States
Amy F.
The price is NZ$417
includes taxes & fees
14 May - 15 May
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

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 NZ$689
includes taxes & fees
11 May - 12 May
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Paradise Palm Unit - #4

Paradise Palm Unit - #4
Harwich
10.0 out of 10, Exceptional, (31 reviews)
"The property was quaint, perfect for a quick weekend getaway."
United States
Kylie S.
The price is NZ$348
includes taxes & fees
12 May - 13 May
Paradise Palm Unit - #4

The Blue Crab Unit 7

The Blue Crab Unit 7
Harwich
9.6 out of 10, Exceptional, (15 reviews)
"Nice place, decent central location "
United States
hannah k.
The price is NZ$330
includes taxes & fees
3 June - 4 June
The Blue Crab Unit 7

Scituate Seaside Escape – Sleeps 8, Walk to Beach

Scituate Seaside Escape – Sleeps 8, Walk to Beach
Scituate
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at this property. The location works very well for weddings at the Barker house and the location to downtown. I would recommend staying here.. "
United States
Rick L.
Scituate Seaside Escape – Sleeps 8, Walk to Beach
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 favorite 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 depends 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 NZ$205 per night. Entering your travel dates in the search wizard you might find 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.