Eastern Massachusetts holiday homes

We found 17,123 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
Paquachuck Inn
the lounge, small event
Exceptional
(6 reviews)

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

Westport Point

8% off
NZ$29,612
for 7 nights, 1 room
NZ$4,230 per night
includes taxes & fees
Relax by the sea! Bed & Breakfast near Horseneck State Beach
New kitchen cabinets, granite counters, refrigerator, exhaust, finished floor
view from Cabbyshack restaurant downtown Plymouth
New three season porch off LR.  Lots of windows with screens-great for breezes!
Steps to front door with keypad lock.  your code
Exceptional
(164 reviews)

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

Plymouth

8% off
NZ$11,370
for 7 nights, 1 home
NZ$1,624 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
Living Room
Bar Counter
Exceptional
(5 reviews)

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

Framingham

12% off
NZ$7,440
for 7 nights, 1 home
NZ$1,063 per night
includes taxes & fees
Lux Colonial Home: Hot tub, Game Room, Home Theatre, Karaoke
Outdoor dining
Exterior
Living area
Living area
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
NZ$1,394
for 7 nights, 1 cottage
NZ$199 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Living room with Smart TV
View from front porch
Private kitchen
Living room
Exceptional
(25 reviews)

Renovated Cottage-- steps away from the water

Tiverton

8% off
NZ$4,716
for 7 nights, 1 cottage
NZ$674 per night
includes taxes & fees
Renovated Cottage-- steps away from the water
The garden
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
NZ$3,160
for 7 nights, 1 home
NZ$451 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Room
Living area
Outdoor dining
Living area
Exceptional
(43 reviews)

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

Boston

8% off
NZ$9,665
for 7 nights, 1 apartment
NZ$1,381 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Large island, comfortable seating area
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

19% off
NZ$10,660
for 7 nights, 1 home
NZ$1,523 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Stocked kitchen
Stocked kitchen
Exterior
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
NZ$3,636
for 7 nights, 1 apartment
NZ$519 per night
includes taxes & fees
Near Old Silver Beach Falmouth-Two bedroom,private bathroom & kitchenette studio
Flowering plantings including blue hydrangea, lilac and magnolia
Deck with teak table and chairs
Kitchen with island
Interior
Exceptional
(93 reviews)

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

Chatham

7% off
NZ$6,508
for 7 nights, 1 home
NZ$930 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Patio garden
Marina
Gracious staircase access to Third Floor
Outdoor dining
Exceptional
(98 reviews)

Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean

Hull

8% off
NZ$3,572
for 7 nights, 1 room
NZ$510 per night
includes taxes & fees
Third Floor Suite in waterfront Victorian on peninsula surrounded by ocean
Dining
The garden gate
Living area
Terrace/patio
Exceptional
(41 reviews)

Walk to private beach from beautiful Abels Hill house

Chilmark

8% off
NZ$9,245
for 7 nights, 1 home
NZ$1,321 per night
includes taxes & fees
Walk to private beach from beautiful Abels Hill house
Interior
Interior
Private kitchen
Interior
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

19% off
NZ$7,863
for 7 nights, 1 home
NZ$1,123 per night
includes taxes & fees
Luxury Loft Historic Center Oak Bluffs
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$4,418
for 7 nights, 1 home
NZ$631 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Portion of garden surrounding my home
View of Spinnaker Island and water from Master Bedroom Suite
Twin bed with trundle bed in second room in Master Bedroom Suite
Staircase from waterfront to my home
Excellent
(47 reviews)

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

Hull

8% off
NZ$3,304
for 7 nights, 1 room
NZ$472 per night
includes taxes & fees
Master Bedroom Suite in Beautiful 1880's Victorian. Spectacular ocean views.
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
(42 reviews)

Sanctuary House: An ocean-view farmhouse retreat

Vineyard Haven

8% off
NZ$8,982
for 7 nights, 1 home
NZ$1,283 per night
includes taxes & fees
Sanctuary House: An ocean-view farmhouse retreat
Exterior
Outdoor dining
Private kitchen
Living area
Exceptional
(128 reviews)

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

Edgartown

7% off
NZ$7,040
for 7 nights, 1 home
NZ$1,006 per night
includes taxes & fees
On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
#2 queen bedroom
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
NZ$6,886
for 7 nights, 1 cottage
NZ$984 per night
includes taxes & fees
Cape Cod Dune Cottage Spectacular Ocean Views, over the dune to a private beach
Private kitchen
Living area
Dining
Exterior detail
Exceptional
(20 reviews)

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

Salem

6% off
NZ$3,522
for 7 nights, 1 apartment
NZ$503 per night
includes taxes & fees
Hocus Pocus Season is here! Don’t miss it!
Property grounds
Living area
Room
Living area
Exceptional
(15 reviews)

Fresh Design-Walk to Salem-Food-Train Station

Beverly

8% off
NZ$2,996
for 7 nights, 1 apartment
NZ$428 per night
includes taxes & fees
Fresh Design-Walk to Salem-Food-Train Station
Private kitchen
Interior
Room
Interior
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
NZ$7,042
for 7 nights, 1 apartment
NZ$1,006 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
Pet Friendly Cape House.
Deck with outdoor dining & plenty of flowers.
Wonderful
(67 reviews)

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

East Falmouth

8% off
NZ$5,581
for 7 nights, 1 home
NZ$797 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.
Out door seating for 8 & gas grill.
Open dining room, living room, kitchen (brand new) 
 & deck.
Wonderful
(35 reviews)

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

East Falmouth

8% off
NZ$5,581
for 7 nights, 1 home
NZ$797 per night
includes taxes & fees
Minutes to Menauhant Beach - July & August AVAILABILITY clubhouse heated pool.
Guest House front view
DOWN TOWN
Sconset Roses
Court yard
Exceptional
(86 reviews)

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

Nantucket

8% off
NZ$10,241
for 7 nights, 1 home
NZ$1,463 per night
includes taxes & fees
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.
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  • All the privacy of home

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

    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 Bookabach 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? Bookabach 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 Bookabach 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, Bookabach 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 Bookabach 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 Bookabach, 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 Bookabach 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.