Southeast Massachusetts Holiday Rentals

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Holiday Rentals in Southeast Massachusetts

Our top choices for Southeast Massachusetts holiday rentals

Sandcastle Resort and Club

3.0 star property
7.4 out of 10, Good, (1106)
"great beach!"
The price is NZ$192
includes taxes & fees
28 Sept - 29 Sept
Sandcastle Resort and Club

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (355)
"Excellent place to stay, near great restaurants and shopping."
Holly Tree Resort

Modern Beachfront Condo, Gorgeous Views and Centrally Located

10.0 out of 10, Exceptional, (53)
"Great property have stayed multiple times. Had a concern and John handled it immediately. Great host and great location. Will book again soon. "
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (286)
"All around a great place to stay!"
The price is NZ$394
includes taxes & fees
23 Oct - 24 Oct
Edgewater Beach Resort, a VRI resort

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (317)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The Cove at Yarmouth by VRI Americas

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (111)
"I only stayed for a night, but I found the property comfortable and quiet and I enjoyed the hot tub."
The price is NZ$288
includes taxes & fees
25 Sept - 26 Sept
Brewster Green Resort

Oceana Cottages

2.5 star property
8.4 out of 10, Very good, (67)
"The location was great, literally right on the water. Check in was easy and the cottage was clean. While the property is older, it was a very pleasant place and the owner was so friendly and helpful."
Oceana Cottages

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (163)
"Overall everything was great. Rooms are clean. Very quiet. The upper outside deck requires repair but my understanding is owners association is aware and addressing. I think its our fourth time there. Keep going back. Only thing is we wished there was an outdoor pool. Would be great on those warm sunny days."
The price is NZ$402
includes taxes & fees
22 Oct - 23 Oct
Riverview Resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (178)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters

Thomas Sea Suites

3.5 star property
9.2 out of 10, Wonderful, (87)
"Everything about our stay was wonderful. Would definitely stay here again!!"
Thomas Sea Suites

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

10.0 out of 10, Exceptional, (281)
"Perfect for a couple!Everything was amazing."
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (129)
"The house is a perfect place to stay. Close to the beach and the town of Hyannis. An ideal location for discovering the Cape Cod area. We felt relaxed and comfortable when we were there."
Steps to the beach with an ocean view,

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

10.0 out of 10, Exceptional, (38)
"Great place for a family get together "
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (223)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (168)
"Beautiful cottage , great location. Would love to stay again "
The price is NZ$1,321
includes taxes & fees
12 Oct - 13 Oct
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

8.8 out of 10, Excellent, (80)
"Great place for the price- no issues that owner couldn’t respond to. Just a little too far from the rest of the family who stayed in walking distance to town. Loved it anyway!"
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.4 out of 10, (30)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Harbourtown Suites

4.0 star property
9.2 out of 10, Wonderful, (69)
"The property was very clean and comfortable. I will definitely book this place again if I’m traveling to Plymouth, MA. "
The price is NZ$728
includes taxes & fees
18 Oct - 19 Oct
Harbourtown Suites

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

9.4 out of 10, Exceptional, (114)
"This property was as advertised. Right on a private beach, the views here are incredible. Make sure you plan to see a sunrise or sunset! Owner is very easy to work with and responsive. "
The price is NZ$2,619
includes taxes & fees
11 Oct - 12 Oct
Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

Cape Cod Bay Home w/ Deck + Private Beach Access

9.6 out of 10, Exceptional, (33)
"I wanted to celebrate my daughter’s completion of her doctoral program with a dream vacation. My sister and two nieces joined us. The home was absolutely beautiful and the ocean view was amazing! We just couldn’t be more pleased with our stay! "
Cape Cod Bay Home w/ Deck + Private Beach Access
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

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$192 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.