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, (1090)
"Right on the beach and Walking distance to downtown"
The price is AU$171
includes taxes & fees
28 Sept - 29 Sept
Sandcastle Resort and Club

Oceana Cottages

2.5 star property
8.2 out of 10, Very good, (62)
"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

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

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (349)
"Very nice place to stay "
Holly Tree Resort

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (314)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The price is AU$379
includes taxes & fees
25 Sept - 26 Sept
The Cove at Yarmouth by VRI Americas

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (283)
"All around a great place to stay!"
The price is AU$409
includes taxes & fees
30 Sept - 1 Oct
Edgewater Beach Resort, a VRI resort

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (107)
"I only stayed for a night, but I found the property comfortable and quiet and I enjoyed the hot tub."
The price is AU$382
includes taxes & fees
28 Sept - 29 Sept
Brewster Green Resort

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 AU$336
includes taxes & fees
7 Sept - 8 Sept
Riverview Resort

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

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (219)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

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

10.0 out of 10, Exceptional, (279)
"Perfect for a couple!Everything was amazing."
The price is AU$2,151
includes taxes & fees
16 Sept - 17 Sept
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

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

10.0 out of 10, Exceptional, (164)
"Beautiful cottage , great location. Would love to stay again "
The price is AU$1,858
includes taxes & fees
26 Sept - 27 Sept
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (127)
"Nice home, great views and very relaxing stay."
Steps to the beach with an ocean view,

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (177)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

9.8 out of 10, Exceptional, (151)
"Adorable cottage just a short walk to town and ferry! "
The price is AU$1,563
includes taxes & fees
3 Oct - 4 Oct
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

Stunning Oceanfront Home With Amazing Views ~ Private Beach

9.6 out of 10, Exceptional, (112)
"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 AU$2,176
includes taxes & fees
21 Sept - 22 Sept
Stunning Oceanfront Home With Amazing Views ~ Private Beach

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

6.4 out of 10, (26)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

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

8.8 out of 10, Excellent, (78)
"Had a great time during our weekend trip to Nantucket. Property was in a great area and close to bus stop to get into town easily. Host was very responsive and easy to get a hold of. Only downsides were that the bathroom floors would get soaked during a shower even with the shower curtain and the basement felt slightly humid/moist. No tv in main living area. Other than those minor things would definitely recommend this property as an affordable option to stay in Nantucket "
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

Mermaid Cottage! beautiful propety!

10.0 out of 10, Exceptional, (102)
"Great property and location!"
Mermaid Cottage! beautiful propety!

Harbourtown Suites

4.0 star property
9.2 out of 10, Wonderful, (67)
"The property was very clean and comfortable. I will definitely book this place again if I’m traveling to Plymouth, MA. "
The price is AU$674
includes taxes & fees
30 Sept - 1 Oct
Harbourtown Suites
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 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$171 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.