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Top 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, (1080)
"great beach!"
The price is £99
includes taxes & fees
21 Sept - 22 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 £257
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, (282)
"All around a great place to stay!"
The price is £228
includes taxes & fees
26 Sept - 27 Sept
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 £177
includes taxes & fees
28 Aug - 29 Aug
Brewster Green 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

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

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 £140
includes taxes & fees
14 Sept - 15 Sept
Riverview Resort

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, (126)
"Nice home, great views and very relaxing stay."
Steps to the beach with an ocean view,

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

10.0 out of 10, Exceptional, (277)
"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 £976
includes taxes & fees
1 Sept - 2 Sept
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

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!!!

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

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 £1,165
includes taxes & fees
21 Sept - 22 Sept
Stunning Oceanfront Home With Amazing Views ~ Private Beach

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 "
The price is £913
includes taxes & fees
26 Sept - 27 Sept
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

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 £917
includes taxes & fees
9 Sept - 10 Sept
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

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

6.2 out of 10, (24)
"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

Harborview Nantucket

4.0 star property
9.6 out of 10, Exceptional, (13)
"We had an excellent stay at harbor view cottages! The property is beautiful and close to everything. it is clear that the owners paid attention to all the little details when furnishing the cottage, which I always appreciate. I will definitely be returning! "
Harborview Nantucket

Private Modern Bedroom In a Central Location

9.4 out of 10, Exceptional, (25)
"He property was beautiful. Very private, clean and plenty of space. The hosts are also super friendly. The property is close to a stop on the Miacomet line of The Wave. It’s about 1.5 miles from the middle of town and 2.5 miles from Surfside."
Private Modern Bedroom In a Central Location
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, apart-hotels, 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 £99 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.