Southeast Massachusetts holiday rentals

We found 14,161 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southeast Massachusetts

Showing deals for:1 Jan - 8 Jan

Bar (on property)
back of the house, from the our dock
Paquachuck Inn
the lounge, small event
Exceptional
(6 reviews)

Relax by the sea! Bed & Breakfast near Horseneck State Beach

Westport Point

8% off
AU$24,000
for 7 nights, 1 room
AU$3,429 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
Garage Entrance_Driveway
Cozy Living Room
Living Room
Privacy Can Be Yours
Exceptional
(11 reviews)

Beachside family POOLSPAOPEN20thAPril

Centerville

12% off
AU$12,457
for 7 nights, 1 home
AU$1,780 per night
includes taxes & fees
Beachside family POOLSPAOPEN20thAPril
New kitchen cabinets, granite counters, refrigerator, exhaust, finished floor
view from Cabbyshack restaurant downtown Plymouth
New fire pit on new patio with raised seating in backyard
Steps to front door with keypad lock.  your code
Exceptional
(165 reviews)

Awesome views of ocean 3 levels! 4 Suites plus! Sleep 16 5 min walk 5.5 baths

Plymouth

8% off
AU$9,292
for 7 nights, 1 home
AU$1,327 per night
includes taxes & fees
Awesome views of ocean 3 levels! 4 Suites plus! Sleep 16 5 min walk 5.5 baths
Staircase from waterfront to my home
View of Spinnaker Island and water from Master Bedroom Suite
Portion of garden surrounding my home
Twin bed with trundle bed in second room in Master Bedroom Suite
Excellent
(48 reviews)

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

Hull

8% off
AU$2,708
for 7 nights, 1 room
AU$387 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Exterior
Outdoor dining
Private kitchen
Dining
Exceptional
(9 reviews)

Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

Edgartown

8% off
AU$9,294
for 7 nights, 1 home
AU$1,328 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown
Out door seating for 8 & gas grill.
Use of clubhouse heated POOL & tennis courts.
Great kayaking down the street to Washburn Island & Waquoit Bay.
Brand new kitchen with stainless & quartz.
Wonderful
(35 reviews)

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

East Falmouth

8% off
AU$4,540
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Newly built cedar and mahogany with rain head shower.
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Large, farmhouse fireplace perfect for chillier seasons.
Dining area can seat 8-10 and looks onto patio and water views.
Exceptional
(43 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off
AU$7,259
for 7 nights, 1 home
AU$1,037 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Master Bedroom - King Bed, TV, Bureau and ensuite bath
Shuffle Board
Living Room
Kitchen, Dining area:  Fridge, Stove, Dishwasher
Exceptional
(138 reviews)

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

Harwich

5% off
AU$3,428
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Master Bedroom tastefully decorated for you.
The Private Beach is just steps away!
Warm fireplace for cold nights
Comfortable living room with hardwood floors.
Exceptional
(124 reviews)

Private Beach on Nantucket Sound - Walk to Beach, Town, Harbor! Free EV Charging

Hyannis

8% off
AU$6,254
for 7 nights, 1 home
AU$893 per night
includes taxes & fees
Private Beach on Nantucket Sound - Walk to Beach, Town, Harbor! Free EV Charging
Private kitchen
Interior
Interior
Interior
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off
AU$6,339
for 7 nights, 1 home
AU$906 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Deck with outdoor dining & plenty of flowers.
Kayaks to paddle around Waquoit Bay to Washburn Island
Slate kitchen island & granite dining room table.
Seating for 10.
Open floor plan of Living Room/ Dining room & Kitchen.
Excellent
(70 reviews)

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

East Falmouth

8% off
AU$4,540
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Living room with cathedral ceiling - open floor plan
Deck with teak table and chairs
Kitchen with island
Interior
Exceptional
(96 reviews)

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham

8% off
AU$5,185
for 7 nights, 1 home
AU$741 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Gracious staircase access to Third Floor
Marina
Patio garden
Outdoor dining
Exceptional
(99 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,926
for 7 nights, 1 room
AU$418 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Living area
The Fog
Entrance
Room
Exceptional
(46 reviews)

Tranquil Oasis: A Beautiful Water-Front Home

Forestdale

7% off
AU$4,526
for 7 nights, 1 home
AU$647 per night
includes taxes & fees
Tranquil Oasis: A Beautiful Water-Front Home
Kitchen & stairs to upper level
Exterior
Kitchen
Living room
Exceptional
(76 reviews)

Beachfront Aquinnah home. Beautiful views!

Aquinnah

8% off
AU$5,964
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Beachfront Aquinnah home. Beautiful views!
#1 Queen bedroom -View from queen bed
sand dune looking down the beach
kitchen sink winter view
#2 queen bedroom
Exceptional
(102 reviews)

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

East Sandwich

7% off
AU$4,170
for 7 nights, 1 cottage
AU$596 per night
includes taxes & fees
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
Back entrance into first floor kitchen, bedroom and bathroom
Stocked kitchen
Exterior
Queen size bed in lower level basement
Very good
(36 reviews)

Near Old Silver Beach Falmouth-Two bedroom,private bathroom & kitchenette studio

North Falmouth

8% off
AU$3,014
for 7 nights, 1 apartment
AU$431 per night
includes taxes & fees
Near Old Silver Beach Falmouth-Two bedroom,private bathroom & kitchenette studio
Dining
Property grounds
Room
Interior
Exceptional
(55 reviews)

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

Aquinnah

8% off
AU$3,257
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Ocen Edge Restaurant
Exterior
Interior
Dining
Exceptional
(12 reviews)

Beautifully renovated second-floor condo at Ocean Edge Resort.

Brewster

16% off
AU$2,186
for 7 nights, 1 apartment
AU$312 per night
includes taxes & fees
Beautifully renovated second-floor condo at Ocean Edge Resort.
Exterior
Living area
Living area
Dining
Exceptional
(80 reviews)

284 - Cozy House with free huge parking

Quincy

8% off
AU$6,992
for 7 nights, 1 home
AU$999 per night
includes taxes & fees
284 - Cozy House with free huge parking
Panoramic  View From Kitchen into Living Area
Retractable Awning protects you from the sun and provides a cozy atmosphere!
Open seats at the bar!
Bedroom w/ Queen Bed
Exceptional
(51 reviews)

Waterfront Condo with Stunning Harbor Views!!

Provincetown

12% off
AU$4,347
for 7 nights, 1 apartment
AU$621 per night
includes taxes & fees
Waterfront Condo with Stunning Harbor Views!!
Outdoor dining
Property grounds
Room
Private kitchen
Exceptional
(93 reviews)

Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach

Aquinnah

8% off
AU$5,609
for 7 nights, 1 home
AU$801 per night
includes taxes & fees
Martha's Vineyard Cozy Getaway Near Picturesque Philbin Beach
Private kitchen
Exterior detail
Living area
Room
Exceptional
(11 reviews)

Gorgeous 3-bedroom house close to Willowbend, New Seabury in charming Mashpee

Mashpee

8% off
AU$8,900
for 7 nights, 1 home
AU$1,271 per night
includes taxes & fees
Gorgeous 3-bedroom house close to Willowbend, New Seabury in charming Mashpee
Landscaping is essential to maintain the gardens
Property grounds
Open floor plan,slider leads to deck w/ Weber barbecue grill and deck  furniture
Room
Exceptional
(49 reviews)

3bedroom private residence on cul de sac near National Seashore

Eastham

7% off
AU$3,590
for 7 nights, 1 home
AU$513 per night
includes taxes & fees
3bedroom private residence on cul de sac near National Seashore
  • 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. 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)
  • Stand Up & Paddle Cape Cod (12 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:

  • 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)
  • East Sandwich Beach (5.8 mi / 9.3 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.