Southeast Massachusetts holiday rentals

We found 14,388 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southeast Massachusetts

Showing deals for:13 Nov - 20 Nov

Steps to front door with keypad lock.  your code
view from Cabbyshack restaurant downtown Plymouth
New kitchen cabinets, granite counters, refrigerator, exhaust, finished floor
New three season porch off LR.  Lots of windows with screens-great for breezes!
Exceptional
(163 reviews)

August dates available!! 4 Suites plus! Sleep 16 5 min walk to beach 5.5 baths

Plymouth

8% off
AU$8,834
for 7 nights, 1 home
AU$1,262 per night
includes taxes & fees
August dates available!! 4 Suites plus! Sleep 16 5 min walk to beach 5.5 baths
Outdoor dining
Exterior
Living area
Private kitchen
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
AU$1,111
for 7 nights, 1 cottage
AU$159 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Exterior
Living area
Private kitchen
Exceptional
(44 reviews)

Shoreline Serenity: Your Coastal Escape

Marshfield

8% off
AU$4,951
for 7 nights, 1 home
AU$707 per night
includes taxes & fees
Shoreline Serenity: Your Coastal Escape
Living area
Interior
Private kitchen
Dining
Very good
(14 reviews)

Charming garden level 1 bedroom 1 bath apartment in Brockton

Brockton

8% off
AU$1,238
for 7 nights, 1 home
AU$177 per night
includes taxes & fees
Charming garden level 1 bedroom 1 bath apartment in Brockton
Exterior
Living area
Living area
Dining table with view of ocean in the sunroom
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

8% off
AU$5,937
for 7 nights, 1 cottage
AU$848 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Interior
Living area
Room
Private kitchen
Very good
(38 reviews)

The Cabin on Chappy!

Edgartown

8% off
AU$3,503
for 7 nights, 1 cottage
AU$500 per night
includes taxes & fees
The Cabin on Chappy!
kitchen sink winter view
sand dune looking down the beach
#1 Queen bedroom -View from queen bed
From the beach
Exceptional
(102 reviews)

Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach

East Sandwich

7% off
AU$4,372
for 7 nights, 1 cottage
AU$625 per night
includes taxes & fees
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
Interior
Interior
Private kitchen
Outdoor dining
Exceptional
(50 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

15% off
AU$8,788
for 7 nights, 1 home
AU$1,255 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Exterior
Private kitchen
Nice deck right off the kitchen with a grill and exterior furniture
Living area
Exceptional
(23 reviews)

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

Falmouth

7% off
AU$4,309
for 7 nights, 1 home
AU$616 per night
includes taxes & fees
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
Master Bedroom - King Bed, TV, Bureau and ensuite bath
Shuffle Board
Living Room
Kitchen, Dining area:  Fridge, Stove, Dishwasher
Exceptional
(137 reviews)

#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat

Harwich

7% off
AU$3,131
for 7 nights, 1 home
AU$447 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Room
Harbor is a 3-5 minute walk from the suite.
Exterior detail
Living area
Exceptional
(25 reviews)

Coastal Private Guest Suite

Cohasset

8% off
AU$2,164
for 7 nights, 1 home
AU$309 per night
includes taxes & fees
Coastal Private Guest Suite
Open floor plan of Living Room/ Dining room & Kitchen.
Kayaks to paddle around Waquoit Bay to Washburn Island
Deck with outdoor dining & plenty of flowers.
Pet Friendly Cape House.
Wonderful
(64 reviews)

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

East Falmouth

8% off
AU$4,420
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Great kayaking down the street to Washburn Island & Waquoit Bay.
Use of clubhouse heated POOL & tennis courts.
Open dining room, living room, kitchen (brand new) 
 & deck.
Out door seating for 8 & gas grill.
Wonderful
(33 reviews)

Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.

East Falmouth

8% off
AU$4,420
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
KING SECOND FLOOR
DEN
SIDE VIEW
KITCHEN
Exceptional
(21 reviews)

Walk to Children's Beach- house w/ Yard + Firepit

Nantucket

8% off
AU$16,731
for 7 nights, 1 home
AU$2,390 per night
includes taxes & fees
Walk to Children's Beach- house w/ Yard + Firepit
Walkway from waterfront to my home at top of stairs
View of Spinnaker Island and water from Master Bedroom Suite
Twin bed with trundle bed in second room in Master Bedroom Suite
Portion of garden surrounding my home
Excellent
(46 reviews)

Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.

Hull

8% off
AU$2,690
for 7 nights, 1 room
AU$384 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Also views of East Harbor!
Living room right on the beach. Come in and relax after sunning on the sand!
With everything you need for your stay!
All linens and towels provided for our guests!
Exceptional
(46 reviews)

Townhouse Beach Front Living - 2BD 3BA - Central AC - Linen Towels provided

North Truro

7% off
AU$4,562
for 7 nights, 1 home
AU$652 per night
includes taxes & fees
Townhouse Beach Front Living - 2BD 3BA - Central AC - Linen Towels provided
Sconset Roses
DOWN TOWN
living room
Court yard
Exceptional
(86 reviews)

OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.

Nantucket

8% off
AU$8,161
for 7 nights, 1 home
AU$1,166 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Interior
Property grounds
Dining
Living area
Exceptional
(53 reviews)

Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!

Aquinnah

8% off
AU$3,182
for 7 nights, 1 home
AU$455 per night
includes taxes & fees
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Fresh Pond
Dining
Living area
Exterior
Exceptional
(8 reviews)

Fresh Pond Cottage! A charming & peaceful getaway for couples or small families.

Plymouth

8% off
AU$3,573
for 7 nights, 1 cottage
AU$510 per night
includes taxes & fees
Fresh Pond Cottage! A charming & peaceful getaway for couples or small families.
Interior
Exterior detail
Dining
Outdoor dining
Exceptional
(41 reviews)

West End Tiny House / Walk to Commercial St

Provincetown

7% off
AU$1,575
for 7 nights, 1 cottage
AU$225 per night
includes taxes & fees
West End Tiny House / Walk to Commercial St
A place to rest your head after all the fun you will have here!
Welcome to the porch where you can relax after a day at the beach or golfing!
Eat in kitchen. Enjoy the lobsters!
Built in microwave and range.
Wonderful
(64 reviews)

Delightful Cottage for Two

Chatham

8% off
AU$2,368
for 7 nights, 1 cottage
AU$338 per night
includes taxes & fees
Delightful Cottage for Two
Private patio with seating for 8. Outdoor shower.
Quiet location with off-street parking for two vehicles. Security camera.
Master Bedroom with access to shared bath, desk, and high-resolution monitor.
Fully-equipped kitchen
Exceptional
(58 reviews)

Beautiful House Minutes from Town, on Bike Path

Nantucket

8% off
AU$9,208
for 7 nights, 1 home
AU$1,315 per night
includes taxes & fees
Beautiful House Minutes from Town, on Bike Path
Exterior detail
Living area
Private kitchen
Dining
Exceptional
(27 reviews)

Steps to the beach!

Dennis Port

8% off
AU$3,545
for 7 nights, 1 cottage
AU$506 per night
includes taxes & fees
Steps to the beach!
Laundry/Back patio
Terrace/patio
Kitchen
North-facing side of house.  NOTE: Outdoor shower on left.
Exceptional
(66 reviews)

Classic Gem! Nothing Like it! Private cottage on Main St.

Nantucket

6% off
AU$8,765
for 7 nights, 1 cottage
AU$1,252 per night
includes taxes & fees
Classic Gem! Nothing Like it! Private cottage on Main St.
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting historical Southeast Massachusetts

The area's history and museums are just some of the reasons to come on holiday to Southeast Massachusetts. Renowned for its seafood restaurants, sporting events and beaches, this city welcomes all visitors. Take in top local attractions such as Gillette Stadium and Cape Cod Beaches. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Southeast Massachusetts

Are you looking for attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that Southeast Massachusetts has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Water Wizz (5.3 mi / 8.5 km)
  • Cape Cod Country Club (8.5 mi / 13.6 km)
  • Pinehills Golf Club (10.1 mi / 16.2 km)
  • Waverly Oaks Golf Club (10.6 mi / 17.1 km)
  • Cape Cod Winery (11.5 mi / 18.4 km)
  • Shining Sea Bikeway (12.1 mi / 19.4 km)

Exploring the beaches and other natural features in Southeast Massachusetts

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Southeast Massachusetts. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Beaches (21.1 mi / 33.9 km)
  • Heritage Museums and Gardens (2.7 mi / 4.3 km)
  • Scusset Beach State Reservation (3.4 mi / 5.5 km)
  • Town Neck Beach (4.1 mi / 6.6 km)
  • Onset Beach (5.3 mi / 8.6 km)
  • Shell Point Beach (5.4 mi / 8.8 km)

Travelling to and around Southeast Massachusetts

The nearest airport is in Plymouth, MA (PYM-Plymouth Municipal), located 14.6 mi (23.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 15 mi (24.1 km) away.

If you prefer to travel by train, Bourne Buzzards Bay Station, Hyannis Transportation Center and Plymouth Station are the main stations in the city. You can see more of Southeast Massachusetts by catching a ride on the metro at Greenbush Station, North Scituate Station or Cohasset Station.

Frequently asked questions

What is the best area to stay in Southeast Massachusetts when booking a holiday home?
Among the most sought-after destinations to book your holiday home in Southeast Massachusetts is Dennis. Spend your trip here and explore its big-ticket attractions, like Cape Cod Museum of Art and Mayflower Beach.
What is the most popular type of holiday home accommodation in Southeast Massachusetts?
Houses are the most popular style of holiday home in Southeast Massachusetts, according to our data. Even if you've got something a little different in mind, Stayz has properties in many shapes and sizes. Explore our options to find your perfect match.
How much does it cost to rent a holiday home in Southeast Massachusetts?
Property type, season and length of stay are among the factors that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy country cottages to plush villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Southeast Massachusetts?
The average price for a holiday home near the beach in Southeast Massachusetts depends on when you're going and the type and size of property you're searching for. Find prices easily and quickly on Stayz by entering your travel dates. Then use the filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, WiFi and air conditioning.
What are popular home amenities in Southeast Massachusetts?
When it comes to home amenities that people look for in Southeast Massachusetts, a microwave oven, a fridge and a stovetop rank highest. With Stayz holiday homes, you'll enjoy choices to suit your taste and style, whether you're going on a holiday with your partner, your friends or even pets.
Are there large group holiday homes in Southeast Massachusetts?
Pick from 1 ,509 holiday properties in Southeast Massachusetts that can host 10 or more guests. Whether you're organising a trip with the family or an event like a birthday party, there's ample space to get your loved ones together under one roof.
What are the top attractions for families in Southeast Massachusetts?
There are plenty of cool things to see and do with the family in Southeast Massachusetts, including:
  • Boston Harbour
  • Wrentham Village Premium Outlets
  • Gillette Stadium
Can I find two-bedroom holiday homes in Southeast Massachusetts?
Southeast Massachusetts has 1 ,668 two-bedroom holiday properties to select from. Enjoy a holiday home with all the space and privacy you want at a price that's hard to resist on Stayz.
Are there holiday homes with WiFi in Southeast Massachusetts?
You'll find 2 ,946 holiday homes with WiFi in Southeast Massachusetts. If you want to disconnect from daily life on your holiday, but still need to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Southeast Massachusetts?
The minimum age is usually 16, 18 or 21. It can differ across properties on Stayz, so check the rules of your chosen Southeast Massachusetts stay before you book.
How long can I rent a holiday home in Southeast Massachusetts for?
How long you can rent a holiday home in Southeast Massachusetts is down to the property. Simply enter your selected travel dates to look at a list of options offering extended stays. With loads of features like air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to discover a perfect place to call your home away from home in Southeast Massachusetts.