Southeast Massachusetts Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Southeast Massachusetts

Property grounds
Sandcastle Resort and Club

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 ￥15,051
￥17,226 total
includes taxes & fees
Nov 10 - Nov 11
Sandcastle Resort and Club
BBQ/picnic area
Edgewater Beach Resort, a VRI resort

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
Front of property
Holly Tree Resort

Holly Tree Resort

3.0 star property
West Yarmouth
9.0 out of 10, Wonderful, (363)
"Yearly trip that makes it all worth it with our stay at the Holly Tree!"
United States
Angel
Holly Tree Resort
Smart TV, stereo
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown
10.0 out of 10, Exceptional, (56)
"Everything about this rental is perfect. Beautiful, clean, well equipped, views, views views!!!!!! Hosts were amazing!!!!! We cannot wait to revisit this special place again!!!!!!!"
United States
Joseph S.
Modern Beachfront Condo, Gorgeous Views and Centrally Located
Indoor pool, outdoor pool
Brewster Green Resort

Brewster Green Resort

3.5 star property
Brewster
9.4 out of 10, Exceptional, (119)
"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 ￥21,325
￥24,406 total
includes taxes & fees
Nov 10 - Nov 11
Brewster Green Resort
Sundeck
Riverview Resort

Riverview Resort

3.0 star property
Bass River
9.2 out of 10, Wonderful, (168)
"The room was big and very clean. The hotel is quaint and quiet. It does not have an elevator which could be an issue for some but we made it work. Overall a great place to stay. Very comfortable and inviting and we loved the amenities."
United States
Kathleen
Riverview Resort
On the beach, white sand
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (191)
"Absolutely beautiful room amenities and view. Hands down the best place we have ever stayed at on the Cape. Definitely going back!!"
United States
Keith
InnSeason Resorts Captain's Quarters
Terrace/patio
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!

Eastham
10.0 out of 10, Exceptional, (27)
"From the moment we arrived we were overtaken by the stunning views and private location. The accommodations and amenities went far beyond our high expectations. David is the ultimate host. He truly assisted us with all aspects of our stay. From changing our dates, to restaurant recommendations his guidance is genuine and compassionate. Thank you David, we appreciate all that you have done for us, and until the next time, may your visits to the Cape give you sunny days, and warm water!"
United States
Don H.
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
Presidential Penthouse | 1 bedroom, premium bedding, down comforters, memory foam beds
Thomas Sea Suites

Thomas Sea Suites

3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (93)
"Great location "
United States
John
Thomas Sea Suites
Exterior
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

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

Nantucket Town
10.0 out of 10, Exceptional, (287)
"Loved this cottage. It was perfect for the two of us plus our puppy. And it was in the perfect location: across the street from the Children's Beach, 4 houses down from the White Elephant and the Brant Point Grill restaurant, and 3 blocks from downtown Nantucket. It was new, spotless, charming and the appliances and accommodations were exemplary. Would definitely stay here again"
United States
Elizabeth M.
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Beach nearby, sun loungers
Steps to the Ocean! Perfect Location!!!

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (230)
"Perfect for a couple and two kids"
United States
Shelly R.
Steps to the Ocean! Perfect Location!!!
Outdoor dining
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

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

Nantucket Town
10.0 out of 10, Exceptional, (176)
"Great place to stay! Walking distance to town and lovely yard to relax in."
United States
Danielle J.
The price is ￥30,646
￥77,933 total
includes taxes & fees
Dec 1 - Dec 2
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
10.0 out of 10, Exceptional, (39)
"The house and property was simply amazing and such a perfect spot for our company team retreat of 12"
United States
Jennifer S.
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Fridge, microwave, stovetop, dishwasher
Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining

Dennis Port
9.0 out of 10, Wonderful, (61)
"Loved our stay in Dennis. The condo was so nice and so clean.. I would certainly consider next summer to revisit. "
United States
Rosemarie P.
The price is ￥9,819
￥44,552 total
includes taxes & fees
Nov 17 - Nov 18
Quaint condo near private beach access with fireplace - close to dining
Exterior
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

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

Nantucket
8.8 out of 10, Excellent, (81)
"Love this property! Has everything we needed. Great location. Close to bike path, beaches and Wave stop. Will definitely be back!"
United States
Michele L.
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
Terrace/patio
Cozy 4 bedroom cottage in town, with parking

Cozy 4 bedroom cottage in town, with parking

2.0 star property
Nantucket Town
9.0 out of 10, Wonderful, (21)
"Loved the location, the outdoor shower, and the fact that we had beach towels and chairs. Tv and internet worked great. No book with house information anywhere. Needed kitchen towels and a few more bath towels. Shower curtain liner needs replaced. Loved nantuckett"
United States
Marcy H.
Cozy 4 bedroom cottage in town, with parking
Exterior
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

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

Oak Bluffs
6.4 out of 10, (31)
"It is an old home that has had no updates. It’s shabby- a little bit of a smell and outdated furniture. That being said, it has everything you need and is a good location on the island, especially if you are driving. It was a deal compared to everything else around and was somehow available during summer with less than 2 months before we booked."
United States
Myrtle A.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Terrace/patio
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
8.2 out of 10, Very Good, (71)
"Beautiful house great views of the river. Peaceful weekend away"
United States
Anthony G.
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Exterior
LUXURIOUS Cottage with Breathtaking Harbor Views

LUXURIOUS Cottage with Breathtaking Harbor Views

Nantucket Town
9.8 out of 10, Exceptional, (171)
"We loved this property and all talked about the next time we can book! The location is perfect and the interior is beautiful. Also super comfy beds!"
United States
Breanne N.
LUXURIOUS Cottage with Breathtaking Harbor Views
Exterior
Free 3rd Night!* New house! Walk to bars/restaurants/harbor, Nantucket in Town!

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

Nantucket Town
9.4 out of 10, Exceptional, (42)
"This home was fantastic for our large group for a long weekend. A 10 minute walk to downtown, the home was immaculate, very spacious (especially the large U-shape sectional in the living room, the kitchen was completely new, and the driveway was large enough for our two large vehicles. The owner was also great to deal with and provided answers to all of our questions. We hope to come back and stay again next year!!!"
United States
Stephen G.
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

Red Jacket Beach Resort

Red Jacket Beach Resort

10/10 Excellent
"Great room, nice view, perfect location. Power did go out one night, coffee machine never worked and they had no fix, and the breakfast is obscenely expensive."
Leila 8-night trip
Posted 1 day ago
Red Jacket Beach Resort

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