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

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

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

Westport Point

8% off
AU$23,979
for 7 nights, 1 room
AU$3,426 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
Steps to front door with keypad lock.  your code
view from Cabbyshack restaurant downtown Plymouth
New three season porch off LR.  Lots of windows with screens-great for breezes!
New kitchen cabinets, granite counters, refrigerator, exhaust, finished floor
Exceptional
(165 reviews)

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

Plymouth

8% off
AU$9,237
for 7 nights, 1 home
AU$1,320 per night
includes taxes & fees
Awesome views of ocean 3 levels! 4 Suites plus! Sleep 16 5 min walk 5.5 baths
Dining
Living area
Exterior
Living area
Exceptional
(80 reviews)

284 - Cozy House with free huge parking

Quincy

8% off
AU$6,986
for 7 nights, 1 home
AU$998 per night
includes taxes & fees
284 - Cozy House with free huge parking
Private kitchen
Interior
Exterior detail
Living area
Exceptional
(33 reviews)

Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41

Quincy

8% off
AU$4,319
for 7 nights, 1 home
AU$617 per night
includes taxes & fees
Spacious Greater Boston 3BR Townhouse Near I-93 • Parking • Pet-Friendly - 41
Living area
Exterior
Private kitchen
Outdoor dining
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
AU$1,117
for 7 nights, 1 cottage
AU$160 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Interior
Living area
Interior
Living area
Exceptional
(5 reviews)

Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35

Randolph

8% off
AU$6,941
for 7 nights, 1 home
AU$992 per night
includes taxes & fees
Luxury & Private 6BR Single House • Summer Retreat w/ Parking & Pet-Friendly 35
Outdoor dining
Marina
Patio garden
Gracious staircase access to Third Floor
Exceptional
(99 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,924
for 7 nights, 1 room
AU$418 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Twin bed with trundle bed in second room in Master Bedroom Suite
View of Spinnaker Island and water from Master Bedroom Suite
Walkway from waterfront to my home at top of stairs
Portion of garden surrounding my home
Excellent
(48 reviews)

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

Hull

8% off
AU$2,706
for 7 nights, 1 room
AU$387 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Living Room
Cozy Living Room
Privacy Can Be Yours
Pool
Exceptional
(11 reviews)

Beachside family POOLSPAOPEN20thAPril

Centerville

12% off
AU$12,447
for 7 nights, 1 home
AU$1,778 per night
includes taxes & fees
Beachside family POOLSPAOPEN20thAPril
Living area
Harbor is a 3-5 minute walk from the suite.
Room
Exterior detail
Exceptional
(28 reviews)

Coastal Private Guest Suite

Cohasset

8% off
AU$2,187
for 7 nights, 1 home
AU$312 per night
includes taxes & fees
Coastal Private Guest Suite
Exterior
Outdoor dining
Interior
Great custom kitchen to meet all of your needs.
Exceptional
(22 reviews)

Escape to Nantucket's charm, just a 6-min drive from Surfside Beach

Nantucket

8% off
AU$6,161
for 7 nights, 1 cottage
AU$880 per night
includes taxes & fees
Escape to Nantucket's charm, just a 6-min drive from Surfside Beach
Dining table with view of ocean in the sunroom
Living area
Living area
Rose covered flower arch next to unit
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

8% off
AU$5,971
for 7 nights, 1 cottage
AU$853 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
Kitchen with island
Deck with teak table and chairs
Flowering plantings including blue hydrangea, lilac and magnolia
Interior
Exceptional
(96 reviews)

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

Chatham

8% off
AU$5,180
for 7 nights, 1 home
AU$740 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
SIDE VIEW
DEN
BACKYARD
KITCHEN
Exceptional
(22 reviews)

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

Nantucket

8% off
AU$23,412
for 7 nights, 1 home
AU$3,345 per night
includes taxes & fees
Walk to Children's Beach- house w/ Yard + Firepit
Interior
Living area
Private kitchen
Property grounds
Exceptional
(35 reviews)

Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA

Duxbury

21% off
AU$2,333
for 7 nights, 1 apartment
AU$333 per night
includes taxes & fees
Cozy 2BR Apartment in Charming Snug Harbor, Duxbury, MA
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$3,408
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Large, farmhouse fireplace perfect for chillier seasons.
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Exterior
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$7,253
for 7 nights, 1 home
AU$1,036 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Guest House front view
DOWN TOWN
living room
Court yard
Exceptional
(86 reviews)

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

Nantucket

8% off
AU$8,209
for 7 nights, 1 home
AU$1,173 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Dining
Outdoor dining
Exterior
Private kitchen
Exceptional
(9 reviews)

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

Edgartown

8% off
AU$9,287
for 7 nights, 1 home
AU$1,327 per night
includes taxes & fees
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown
Private kitchen
Interior
Interior
Interior
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off
AU$6,334
for 7 nights, 1 home
AU$905 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Kitchen & stairs to upper level
Exterior
Living room
Kitchen
Exceptional
(76 reviews)

Beachfront Aquinnah home. Beautiful views!

Aquinnah

8% off
AU$5,959
for 7 nights, 1 home
AU$851 per night
includes taxes & fees
Beachfront Aquinnah home. Beautiful views!
kitchen sink winter view
sand dune looking down the beach
From the beach
#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$4,125
for 7 nights, 1 cottage
AU$589 per night
includes taxes & fees
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
Dining
Heated Swimming pool featuring a saltwater chlorinating system for a more refreshing experience!
Living area
View when you enter the house, walkout deck to the right.
Very good
(40 reviews)

Four Bedroom House on Campground/Retreat!

South Yarmouth

8% off
AU$5,007
for 7 nights, 1 home
AU$715 per night
includes taxes & fees
Four Bedroom House on Campground/Retreat!
Dining
Interior
Private kitchen
Exterior
Exceptional
(7 reviews)

Walk to ferry, town and beaches!

Nantucket

9% off
AU$19,095
for 7 nights, 1 home
AU$2,728 per night
includes taxes & fees
Walk to ferry, town and beaches!
  • 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.