Southeast Massachusetts Holiday Rentals

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Holiday Rentals in Southeast Massachusetts

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (336)
"Nice amenities. "
United States
William
The Club at New Seabury

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (118)
"I only stayed for a night, but I found the property comfortable and quiet and I enjoyed the hot tub."
United States
Jessica
The price is NZ$283
includes taxes & fees
10 Nov - 11 Nov
Brewster Green Resort

Sandcastle Resort and Club

3.0 star property
Provincetown
7.4 out of 10, Good, (1141)
"Very nice place in front of the beach, beautiful view whole year round ☀️🌊"
United States
Maria
The price is NZ$200
includes taxes & fees
10 Nov - 11 Nov
Sandcastle Resort and Club

7 Mi to Downtown Providence: Quiet Apt in Seekonk

3.0 star property
Seekonk
8.0 out of 10, Very good, (1)
"This was a lovely spot to stay with my dog for a bit. Very clean and tidy. Would stay again"
United States
Kristin
The price is NZ$565
includes taxes & fees
10 Nov - 11 Nov
7 Mi to Downtown Providence: Quiet Apt in Seekonk

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (10)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
United States
christine l.
The price is NZ$667
includes taxes & fees
10 Nov - 11 Nov
Charming cottage overlooking the bay in Padanaram Village.

Edgewater Beach Resort, a VRI resort

3.5 star property
Dennis Port
8.8 out of 10, Excellent, (290)
"All around a great place to stay!"
United States
Samantha
Edgewater Beach Resort, a VRI resort

🦀Waterfront at The Velvet Crab~Amazing Sunsets

Eastham
9.8 out of 10, Exceptional, (23)
"Nice little cottage."
United States
Lisa I.
The price is NZ$762
includes taxes & fees
23 Nov - 24 Nov
🦀Waterfront at The Velvet Crab~Amazing Sunsets

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth
10.0 out of 10, Exceptional, (129)
"Numerous options of comfortable seating to enjoy great open ocean view. "
United States
Jen
The price is NZ$681
includes taxes & fees
11 Nov - 12 Nov
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

Plymouth
10.0 out of 10, Exceptional, (18)
"Very nice place. I’d stay there again!"
United States
Jamie C.
The price is NZ$812
includes taxes & fees
25 Nov - 26 Nov
Santorini*themed*priv. yard*near beach* firepit*outdoor shwr

Make this charming, modern retreat your home away from home!!

Wareham
9.6 out of 10, Exceptional, (5)
"Great place for a weekend near family. "
United States
Z B.
The price is NZ$552
includes taxes & fees
11 Nov - 12 Nov
Make this charming, modern retreat your home away from home!!

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Onset
9.8 out of 10, Exceptional, (27)
"Excellent location! Right in the center of everything. The apartment was clean, the view was beautiful and communication was on point! We absolutely will return! Thank you for sharing your home with us. "
United States
Naomi H.
The price is NZ$747
includes taxes & fees
10 Nov - 11 Nov
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

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

Chatham
9.6 out of 10, Exceptional, (29)
"Great visit! Clean property a bit tucked in the woods but overall close to everything and a great spot for the price!"
United States
Christian B.
The price is NZ$608
includes taxes & fees
1 Dec - 2 Dec
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (140)
"We had a fabulous visit!"
United States
Joelle
The price is NZ$288
includes taxes & fees
10 Nov - 11 Nov
Sea Mist Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort

Harwich
9.8 out of 10, Exceptional, (11)
"Friends and I really enjoyed the stay, however short it was. Jen was a great host, very responsive and knowledgable about the area and made the stay feel so stress-free and fun. Would absolutely recommend!"
United States
Jack F.
The price is NZ$967
includes taxes & fees
14 Nov - 15 Nov
Cozy Large Home in Harwich with Patio near Wequassett Resort

Harborview Nantucket

4.0 star property
Nantucket Town
9.6 out of 10, Exceptional, (14)
"Harborview is absolutely fabulous ! The location, the views, the beautiful 1 bedroom we stayed in was so comfortable.. just perfect and The caretakers were so kind ..just heavenly !!"
United States
Eileen
The price is NZ$1,192
includes taxes & fees
10 Nov - 11 Nov
Harborview Nantucket

Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!

Nantucket Town
9.8 out of 10, Exceptional, (60)
"We loved the house and appreciated the location too"
United States
Diane L.
The price is NZ$885
includes taxes & fees
2 Dec - 3 Dec
Luxurious Harbor View "Lilly" Cottage! Walk & Bike To Everything!

Charming 1-Bedroom/bathroom Cottage, Center of Town, parking and outdoor space

Provincetown
9.6 out of 10, Exceptional, (10)
"Right near the heart of town! We really enjoyed our stay!"
United States
Anonymous traveller
Charming 1-Bedroom/bathroom Cottage, Center of Town, parking and outdoor space

Thomas Sea Suites

3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (93)
"Booked the hotel on a Sunday night, had to cancel Monday morning. No refund, no credit towards different dates. Was hesitant about booking it, now I know "
United States
Anthony
Thomas Sea Suites

Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!

Nantucket Town
9.8 out of 10, Exceptional, (62)
"This rental is perfection: it is clean, sizable, spa like, perfect location with beach across the street and walking to town, and has the full Nantucket feel. We spent a few nights as a sisters get away and can’t wait to plan our next trip back!"
United States
Meghan L.
The price is NZ$903
includes taxes & fees
1 Dec - 2 Dec
Luxurious Harbor View “Cindy” Cottage. Walk & Bike To Everything!

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet
10.0 out of 10, Exceptional, (74)
"Drew was one of the best landlords we’ve ever had on a vacation property. He was very responsive to the few questions that we had and asked proactively if there was anything that we needed throughout our week. The view from the porch was spectacular."
United States
David M.
The price is NZ$770
includes taxes & fees
10 Nov - 11 Nov
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
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

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$200 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.