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, (1081)
"great beach!"
The price is AU$172
includes taxes & fees
28 Sept - 29 Sept
Sandcastle Resort and Club

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, (313)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The price is AU$517
includes taxes & fees
19 Sept - 20 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$406
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$383
includes taxes & fees
28 Sept - 29 Sept
Brewster Green Resort

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (162)
"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$334
includes taxes & fees
14 Sept - 15 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

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

10.0 out of 10, Exceptional, (278)
"What a perfect vacation spot. The home was perfect for two and well-appointed. Close to town and dining. Wonderful treasures to find on a walk. Would certainly book for our next trip to Nantucket. "
The price is AU$1,989
includes taxes & fees
1 Sept - 2 Sept
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

Charming Nantucket Escape - Spacious Home w/ Private Yard, Deck & Bonus Loft

"Great, new build home that is spacious and comfortable. Located close to the airport and two bus routes, it is surprisingly accessible even without a vehicle. The beds are the most comfortable we have had on the island, greatly appreciated. Beach supplies such as chairs, umbrellas, and towels were new/like new and made our time at the ocean incredibly enjoyable. We will definitely consider staying here again. "
Charming Nantucket Escape - Spacious Home w/ Private Yard, Deck & Bonus Loft

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,

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

10.0 out of 10, Exceptional, (162)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters

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$2,375
includes taxes & fees
21 Sept - 22 Sept
Stunning Oceanfront Home With Amazing Views ~ Private Beach

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$1,870
includes taxes & fees
10 Sept - 11 Sept
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

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

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, (65)
"We loved the place, location. The place was very clean. We think the WiFi was spot as we were unable to use the TV. We would definately go back."
The price is AU$676
includes taxes & fees
30 Sept - 1 Oct
Harbourtown Suites

Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!

9.4 out of 10, Exceptional, (41)
"We stayed at 8 Atlantic Avenue for the Daffodil Festival weekend. The home is impeccable and beautiful - spacious with gorgeous hardwood floors and a kitchen meant for entertaining. Close to town for shopping and restaurants. Owners were a pleasure to work with and I would highly recommend this property! We loved every aspect of our stay and will definitely rent there again."
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!
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$172 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.