Holiday Rentals in Southeast Massachusetts

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southeast Massachusetts holiday rentals

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Chatham
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is €284
includes taxes & fees
4 Jan - 5 Jan
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

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, (129)
"Very clean and nice place for two for a quick peaceful stay. Great location."
United States
Michele G.
The price is €335
includes taxes & fees
3 Jan - 4 Jan
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (341)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (193)
"Best scenery ever !"
United States
Jacqueline
The price is €126
includes taxes & fees
4 Jan - 5 Jan
InnSeason Resorts Captain's Quarters

Save now for Stroll and winter! Charming cottage, close to lower Main Street.

Save now for Stroll and winter! Charming cottage, close to lower Main Street.
Nantucket Town
10.0 out of 10, Exceptional, (118)
"Terrific cottage filled with great light and decorated with quaint Nantucket Charm!Comfortable sleigh bed with a large TV in the room, with an attached spacious bathroom with washer and dryer!Ideal location in town and a spacious parking spot! "
United States
kristin v.
The price is €290
includes taxes & fees
4 Jan - 5 Jan
Save now for Stroll and winter! Charming cottage, close to lower Main Street.

Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (97)
"Great room & views"
United States
Al
Thomas Sea Suites

Charming 2-bedroom apartment with WiFi, AC in superb Canton

Charming 2-bedroom apartment with WiFi, AC in superb Canton
Canton
9.8 out of 10, Exceptional, (16)
"The house was perfect "
United States
Bendjie
The price is €193
includes taxes & fees
14 Jan - 15 Jan
Charming 2-bedroom apartment with WiFi, AC in superb Canton

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)
"Fun spot for the family or a group. Simple, but clean and themed well. "
United Kingdom
Kyle J.
The price is €362
includes taxes & fees
2 Jan - 3 Jan
Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Love Sand, Madaket on the Beach, Lovely Seaside Home

Love Sand, Madaket on the Beach, Lovely Seaside Home
Nantucket
9.8 out of 10, Exceptional, (56)
"Great location and overall experience. "
United States
Michael S.
The price is €714
includes taxes & fees
16 Jan - 17 Jan
Love Sand, Madaket on the Beach, Lovely Seaside Home

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is €364
includes taxes & fees
4 Jan - 5 Jan
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Stylish 2nd floor Ocean Edge condo

Stylish 2nd floor Ocean Edge condo
Brewster
9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
The price is €370
includes taxes & fees
2 Jan - 3 Jan
Stylish 2nd floor Ocean Edge condo

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
New Seabury
10.0 out of 10, Exceptional, (79)
"We were extremely happy with our stay. The condo was beautiful, had everything we needed. Looking forward to coming back again next year for a longer stay"
United States
Beth H.
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

383-Spacious NEW townhouse 7 beds 3 baths 20’To Boston

383-Spacious NEW townhouse 7 beds 3 baths 20’To Boston
Quincy
9.6 out of 10, Exceptional, (44)
"Beautiful home! Neighborhood is a little older, but the property is beautiful and close to Boston!"
United States
Christopher S.
The price is €358
includes taxes & fees
6 Jan - 7 Jan
383-Spacious NEW townhouse 7 beds 3 baths 20’To Boston

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)
"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 €339
includes taxes & fees
4 Jan - 5 Jan
Anchors Away Inn 2 Br Apt 1 min walk to the Beach King & Queen

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is €342
includes taxes & fees
4 Jan - 5 Jan
Charming cottage overlooking the bay in Padanaram Village.

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Falmouth
8.2 out of 10, Very good, (24)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is €175
includes taxes & fees
8 Jan - 9 Jan
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
Quincy
9.2 out of 10, Wonderful, (36)
"property was as described, very clean and remodeled. Owner was a pleasure to deal with. Would stay again in the future. "
United States
Andrew A.
The price is €366
includes taxes & fees
7 Jan - 8 Jan
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
Nantucket Town
10.0 out of 10, Exceptional, (72)
"Great location just a short walk to the shops, restaurants, and bars. The house was newly updated and very comfortable."
United States
Michael G.
The price is €432
includes taxes & fees
4 Jan - 5 Jan
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

The Charming Gem Near The Water!

The Charming Gem Near The Water!
New Bedford
9.6 out of 10, Exceptional, (34)
"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 €198
includes taxes & fees
18 Jan - 19 Jan
The Charming Gem Near The Water!
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.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 €126 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.