Eastern Massachusetts holiday rentals

We found 17,121 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Eastern Massachusetts

Showing deals for:18 Dec - 25 Dec

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

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

Westport Point

8% off
AU$23,764
for 7 nights, 1 room
AU$3,395 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
New three season porch off LR.  Lots of windows with screens-great for breezes!
view from Cabbyshack restaurant downtown Plymouth
Steps to front door with keypad lock.  your code
New fire pit on new patio with raised seating in backyard
Exceptional
(164 reviews)

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

Plymouth

8% off
AU$9,033
for 7 nights, 1 home
AU$1,290 per night
includes taxes & fees
Awesome views of ocean 3 levels! 4 Suites plus! Sleep 16 5 min walk 5.5 baths
Living Room
Bedroom 1 (Level 2): 1 King bed + ensuite full bath
Bar Counter
Kitchen
Exceptional
(5 reviews)

Lux Colonial Home: Hot tub, Game Room, Home Theatre, Karaoke

Framingham

12% off
AU$5,930
for 7 nights, 1 home
AU$847 per night
includes taxes & fees
Lux Colonial Home: Hot tub, Game Room, Home Theatre, Karaoke
Outdoor dining
Exterior
Private kitchen
Living area
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
AU$1,107
for 7 nights, 1 cottage
AU$158 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Living room
View from front porch
Living room with Smart TV
Private kitchen
Exceptional
(25 reviews)

Renovated Cottage-- steps away from the water

Tiverton

8% off
AU$3,794
for 7 nights, 1 cottage
AU$542 per night
includes taxes & fees
Renovated Cottage-- steps away from the water
Interior
Terrace/patio
Marina
Chestnut Sweet's front door on the garden. The Sweet is in its own building.
Exceptional
(155 reviews)

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead

8% off
AU$2,564
for 7 nights, 1 home
AU$366 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Outdoor dining
Living area
Private kitchen
Living area
Exceptional
(43 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
AU$7,673
for 7 nights, 1 apartment
AU$1,096 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Light & bright second floor great room
Deeded access to nearby Mill Pond to launch your Kayak
Well equipped chef's kitchen w. stainless steel appliances
Fabulous family room, a magnet for family gatherings
Exceptional
(121 reviews)

Water View-Walk town/beach, pets considered, Linen Option

Chatham

20% off
AU$8,574
for 7 nights, 1 home
AU$1,225 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Stocked kitchen
Stocked kitchen
Back entrance into first floor kitchen, bedroom and bathroom
Queen size bed in lower level basement
Very good
(35 reviews)

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

North Falmouth

8% off
AU$2,950
for 7 nights, 1 apartment
AU$421 per night
includes taxes & fees
Near Old Silver Beach Falmouth-Two bedroom,private bathroom & kitchenette studio
Kitchen with island
Deck with teak table and chairs
Interior
Flowering plantings including blue hydrangea, lilac and magnolia
Exceptional
(93 reviews)

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

Chatham

7% off
AU$5,236
for 7 nights, 1 home
AU$748 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Gracious staircase access to Third Floor
Marina
Outdoor dining
View of waterfront from Third Floor Suite Living Room
Exceptional
(98 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
AU$2,897
for 7 nights, 1 room
AU$414 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Living area
The garden gate
Exterior
Dining
Exceptional
(41 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off
AU$7,337
for 7 nights, 1 home
AU$1,048 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Outdoor dining
Interior
Interior
Interior
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off
AU$6,277
for 7 nights, 1 home
AU$897 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
Portion of garden surrounding my home
View of Spinnaker Island and water from Master Bedroom Suite
Staircase from waterfront to my home
Walkway from waterfront to my home at top of stairs
Excellent
(47 reviews)

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

Hull

8% off
AU$2,682
for 7 nights, 1 room
AU$383 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
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$3,557
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Dining area can seat 8-10 and looks onto patio and water views.
Meals on the patio are a daily delight- sparkly mornings to ocean dipped sunsets
Exterior
Large, farmhouse fireplace perfect for chillier seasons.
Exceptional
(42 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off
AU$7,188
for 7 nights, 1 home
AU$1,027 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Private kitchen
Outdoor dining
Living area
Exterior
Exceptional
(128 reviews)

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

Edgartown

7% off
AU$5,603
for 7 nights, 1 home
AU$800 per night
includes taxes & fees
On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
From the beach
sand dune looking down the beach
#1 Queen bedroom -View from queen bed
#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$5,476
for 7 nights, 1 cottage
AU$782 per night
includes taxes & fees
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
Exterior detail
Living area
Private kitchen
Room
Exceptional
(20 reviews)

Hocus Pocus Season is here! Don’t miss it!

Salem

6% off
AU$2,857
for 7 nights, 1 apartment
AU$408 per night
includes taxes & fees
Hocus Pocus Season is here! Don’t miss it!
Living area
Living area
Room
Property grounds
Exceptional
(15 reviews)

Fresh Design-Walk to Salem-Food-Train Station

Beverly

7% off
AU$2,465
for 7 nights, 1 apartment
AU$352 per night
includes taxes & fees
Fresh Design-Walk to Salem-Food-Train Station
Room
Interior
Private kitchen
Interior
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,603
for 7 nights, 1 apartment
AU$800 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Slate kitchen island & granite dining room table.
Seating for 10.
Kayaks to paddle around Waquoit Bay to Washburn Island
Deck with outdoor dining & plenty of flowers.
Open floor plan of Living Room/ Dining room & Kitchen.
Wonderful
(67 reviews)

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

East Falmouth

8% off
AU$4,405
for 7 nights, 1 home
AU$629 per night
includes taxes & fees
Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Open dining room, living room, kitchen (brand new) 
 & deck.
Use of clubhouse heated POOL & tennis courts.
Brand new kitchen with stainless & quartz.
Out door seating for 8 & gas grill.
Wonderful
(35 reviews)

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

East Falmouth

8% off
AU$4,405
for 7 nights, 1 home
AU$629 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Court yard
DOWN TOWN
Guest House front view
Sconset Roses
Exceptional
(86 reviews)

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

Nantucket

8% off
AU$8,135
for 7 nights, 1 home
AU$1,162 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
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    Enjoy full kitchens, laundry, pools, gardens and more
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    More space, more privacy, more amenities — more value

The historical area of Eastern Massachusetts awaits your stay

Come and experience Eastern Massachusetts and its history, museums and entertainment. This city's sporting events, seafood restaurants and university setting draw many visitors. Gillette Stadium and Fenway Park are just a couple of the must-see attractions. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Eastern Massachusetts

Are you hoping to discover attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Eastern Massachusetts a fun place to get away to. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • King Richard's Faire (9.9 mi / 15.9 km)
  • Waverly Oaks Golf Club (10.1 mi / 16.3 km)
  • Rockland Ice Rink (11 mi / 17.7 km)
  • Edaville (11.1 mi / 17.8 km)
  • Pinehills Golf Club (11.2 mi / 18 km)
  • Water Wizz (17.8 mi / 28.6 km)

Exploring the natural features in Eastern Massachusetts

Whether you're an active traveller or just want to appreciate the scenery, Eastern Massachusetts is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (29.3 mi / 47.2 km)
  • Boston Harbor (29.3 mi / 47.2 km)
  • Copley Square (29.3 mi / 47.2 km)
  • Plymouth Harbor (5 mi / 8 km)
  • Duxbury Beach Park (5.7 mi / 9.2 km)
  • Plymouth Long Beach (6.4 mi / 10.2 km)

How to get to and around Eastern Massachusetts

Fly into New Bedford, MA (EWB-New Bedford Regional), the closest airport, located 25.7 mi (41.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Provincetown, MA (PVC-Provincetown Municipal), which is 27.2 mi (43.7 km) away.

If you're travelling by train, Kingston Station, Plymouth Station and Halifax Station are the main stations in the city. It's easy to get around Eastern 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 Eastern Massachusetts when booking a holiday home?
One of the most popular destinations to book your Stayz holiday property in Eastern Massachusetts is Dennis. Spend your trip here and discover its much-loved attractions, like Cape Cod Museum of Art and Mayflower Beach.
What is the most popular type of holiday home accommodation in Eastern Massachusetts?
The most in-demand types of holiday homes in Eastern Massachusetts are houses. Looking for something different? Stayz offers a variety of options to match our guests' unique requirements, so you'll see holiday properties in lots of shapes and sizes. The ideal fit is ready and waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Eastern Massachusetts?
The average price for a holiday home in Eastern Massachusetts is based on a number of factors, such as length of stay, season and property type. Whether you're looking for a sprawling house with room for friends and family or a comfy cabin just enough for two, just enter your dates of travel to find stays with great value.
How much does it cost to rent a beach house in Eastern Massachusetts?
The average price for a holiday home close to the beach in Eastern Massachusetts will depend on when you're going and the type and size of property you want. You can easily find prices on Stayz by entering your dates of travel. Then use our handy 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 Eastern Massachusetts?
Some of the most popular home amenities people are looking for in Eastern Massachusetts include a fridge, a stovetop and a microwave oven. Whether you're on the road with friends, family or even pets, Stayz holiday homes have the best amenities for making new memories with the people who matter most.
Are there large group holiday homes in Eastern Massachusetts?
Eastern Massachusetts has 1 ,674 holiday homes that can host 10 or more guests. These properties come with the space you need to enjoy good times with loved ones.
What are the top attractions for families in Eastern Massachusetts?
Keep your kids busy at these leading family-friendly attractions in Eastern Massachusetts:
  • Fenway Park
  • Boston Common
  • TD Garden
Can I find two-bedroom holiday homes in Eastern Massachusetts?
Choose from 2 ,245 two-bedroom homes in Eastern Massachusetts. Put the kids in the second room or maybe fill it with a couple of your besties. There's a spot for whoever's lucky enough to be coming along.
Are there holiday homes with WiFi in Eastern Massachusetts?
Whether you want to keep up with the news, send some emails or surf social media, there are 3 ,521 holiday homes with WiFi in Eastern Massachusetts. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How old do you have to be to rent a holiday home in Eastern Massachusetts?
Age restrictions can differ between properties on Stayz, so double-check the rules of the holiday home in Eastern Massachusetts you're interested in. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Eastern Massachusetts for?
It all depends on the Eastern Massachusetts property. To browse a list of options offering extended stays, just type your dates and number of guests into the Stayz search page. You can enjoy having the whole place to yourself, along with comforts such as a full kitchen, air conditioning and an outdoor space where the kids can run around and play. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.