Southeast Massachusetts holiday homes

We found 14,322 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southeast Massachusetts

Showing deals for:18 Dec - 25 Dec

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

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

Westport Point

8% off
NZ$29,146
for 7 nights, 1 room
NZ$4,164 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
Outdoor dining
Exterior
Living area
Private kitchen
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
NZ$1,372
for 7 nights, 1 cottage
NZ$196 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Back entrance into first floor kitchen, bedroom and bathroom
Stocked kitchen
Queen size bed in lower level basement
Exterior
Very good
(35 reviews)

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

North Falmouth

8% off
NZ$3,579
for 7 nights, 1 apartment
NZ$511 per night
includes taxes & fees
Near Old Silver Beach Falmouth-Two bedroom,private bathroom & kitchenette studio
Beach
Exterior
Room
Private kitchen
Exceptional
(11 reviews)

Newly renovated Cottage Across the street from Craigville Beach.

Centerville

20% off
NZ$3,542
for 7 nights, 1 cottage
NZ$506 per night
includes taxes & fees
Newly renovated Cottage Across the street from Craigville Beach.
Living room with cathedral ceiling - open floor plan
Deck with teak table and chairs
Kitchen with island
Flowering plantings including blue hydrangea, lilac and magnolia
Exceptional
(92 reviews)

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

Chatham

7% off
NZ$6,406
for 7 nights, 1 home
NZ$915 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Outdoor dining
Marina
Gracious staircase access to Third Floor
Patio garden
Exceptional
(98 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
NZ$3,515
for 7 nights, 1 room
NZ$502 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
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
NZ$4,898
for 7 nights, 1 home
NZ$700 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Walkway from waterfront to my home at top of stairs
View of Spinnaker Island and water from Master Bedroom Suite
Staircase from waterfront to my home
Twin bed with trundle bed in second room in Master Bedroom Suite
Excellent
(47 reviews)

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

Hull

8% off
NZ$3,252
for 7 nights, 1 room
NZ$465 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
Outdoor dining
Interior
Interior
Private kitchen
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off
NZ$7,740
for 7 nights, 1 home
NZ$1,106 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Exterior
Abels Hill Beach
The garden gate
Dining
Exceptional
(39 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off
NZ$9,100
for 7 nights, 1 home
NZ$1,300 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Exterior
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Newly built cedar and mahogany with rain head shower.
Large, farmhouse fireplace perfect for chillier seasons.
Exceptional
(42 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off
NZ$8,840
for 7 nights, 1 home
NZ$1,263 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Living area
Outdoor dining
Living area
Private kitchen
Exceptional
(127 reviews)

On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!

Edgartown

7% off
NZ$6,929
for 7 nights, 1 home
NZ$990 per night
includes taxes & fees
On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
Dining table with view of ocean in the sunroom
Living area
Exterior
Living area
Exceptional
(39 reviews)

Maushop Village Getaway with Ocean Views, Steps to Private Beach

Mashpee

8% off
NZ$7,311
for 7 nights, 1 cottage
NZ$1,044 per night
includes taxes & fees
Maushop Village Getaway with Ocean Views, Steps to Private Beach
kitchen sink winter view
sand dune looking down the beach
#2 queen bedroom
From the beach
Exceptional
(102 reviews)

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

East Sandwich

7% off
NZ$6,778
for 7 nights, 1 cottage
NZ$968 per night
includes taxes & fees
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
Interior
Exterior
Living area
Private kitchen
Wonderful
(5 reviews)

Newly Renovated Chatham Home overlooking Cranberry Bog.

West Chatham

7% off
NZ$8,336
for 7 nights, 1 home
NZ$1,191 per night
includes taxes & fees
Newly Renovated Chatham Home overlooking Cranberry Bog.
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.
Pet Friendly Cape House.
Wonderful
(66 reviews)

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

East Falmouth

8% off
NZ$5,493
for 7 nights, 1 home
NZ$785 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Brand new kitchen with stainless & quartz.
Use of clubhouse heated POOL & tennis courts.
Great kayaking down the street to Washburn Island & Waquoit Bay.
Out door seating for 8 & gas grill.
Wonderful
(35 reviews)

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

East Falmouth

8% off
NZ$5,493
for 7 nights, 1 home
NZ$785 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Court yard
DOWN TOWN
Sconset Roses
Guest House front view
Exceptional
(86 reviews)

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

Nantucket

8% off
NZ$10,079
for 7 nights, 1 home
NZ$1,440 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
Dining Room
Kitchen
Front porch
Kitchen/Living Room area
Exceptional
(32 reviews)

Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.

Falmouth

8% off
NZ$8,074
for 7 nights, 1 home
NZ$1,153 per night
includes taxes & fees
Across the street from Old Silver Beach; New house with hot tub. Sleeps 12.
Front entrance on Angola street
Dinning area and kitchen.  Open floor plan 2nd floor
Mid level entrance with stairs to back terrace
Mid level entrance - up to living room down to 1st floor suite.
Exceptional
(91 reviews)

Charming home tucked on a lovely lane - 10 min walk to main street

Nantucket

8% off
NZ$18,825
for 7 nights, 1 home
NZ$2,689 per night
includes taxes & fees
Charming home tucked on a lovely lane - 10 min walk to main street
Living area
Property grounds
Room
Dining
Exceptional
(55 reviews)

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

Aquinnah

8% off
NZ$3,943
for 7 nights, 1 home
NZ$563 per night
includes taxes & fees
Amazing Views!!! Sunsets!!! Larger Roof Deck!!! Historic Martha’s Vineyard Gem!!
Dining
Exterior detail
Outdoor dining
Interior
Exceptional
(41 reviews)

West End Tiny House / Walk to Commercial St

Provincetown

7% off
NZ$2,055
for 7 nights, 1 cottage
NZ$294 per night
includes taxes & fees
West End Tiny House / Walk to Commercial St
Exterior
Marina
Quaint village of Sconset
Dining
Exceptional
(68 reviews)

Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ

Nantucket

8% off
NZ$5,912
for 7 nights, 1 home
NZ$845 per night
includes taxes & fees
Cute, Quiet, Comfortable, Centrally Located, Outdoor Shower, Large Yard, BBQ
Private kitchen
Dining
Exterior
Fresh Pond
Exceptional
(10 reviews)

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

Plymouth

12% off
NZ$3,636
for 7 nights, 1 cottage
NZ$519 per night
includes taxes & fees
Fresh Pond Cottage! A charming & peaceful getaway for couples or small families.
  • 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, Bookabach 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 Bookabach 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 Bookabach 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 Bookabach 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 Bookabach.
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 Bookabach.
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 Bookabach, 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.

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