Eastham holiday rentals

We found 2,495 holiday rentals — enter your dates for availability
Select from 296 homes, 72 cottages and other holiday rentals in Eastham to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Eastham

Showing deals for:29 Jan - 5 Feb

Living area
Exceptional
(20 reviews)

Sunset Views - Cape Cod Bay.

Eastham

8% off
S$7,893
for 7 nights, 1 home
S$1,128 per night
includes taxes & fees
Sunset Views - Cape Cod Bay.
Exterior
Exceptional
(65 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
S$10,456
for 7 nights, 1 home
S$1,494 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Private kitchen
Exceptional
(8 reviews)

Cape Home w/Oceanview, Roof Deck Pool & Hot Tub

Wellfleet

11% off
S$13,642
for 7 nights, 1 home
S$1,949 per night
includes taxes & fees
Cape Home w/Oceanview, Roof Deck Pool & Hot Tub
Deeded access to nearby Mill Pond to launch your Kayak
Exceptional
(123 reviews)

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

Chatham

30% off
S$6,227
for 7 nights, 1 home
S$890 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Outdoor dining
Exceptional
(54 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
S$20,976
for 7 nights, 1 home
S$2,997 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Private kitchen
Exceptional
(13 reviews)

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

Dennis

7% off
S$3,886
for 7 nights, 1 home
S$555 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Backyard view of house
Exceptional
(32 reviews)

Immaculately maintained, large beach home with heated swimming pool

Eastham

8% off
S$7,525
for 7 nights, 1 home
S$1,075 per night
includes taxes & fees
Immaculately maintained, large beach home with heated swimming pool
Sunny living space with large balcony, and spectacular views to the ocean.
Exceptional
(67 reviews)

SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor

Chatham

8% off
S$12,071
for 7 nights, 1 home
S$1,724 per night
includes taxes & fees
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Living Room & Screen Porch
Exceptional
(54 reviews)

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham

8% off
S$19,473
for 7 nights, 1 home
S$2,782 per night
includes taxes & fees
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Private beach/dock area
Exceptional
(19 reviews)

Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

South Chatham

8% off
S$9,274
for 7 nights, 1 home
S$1,325 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Pottery Barn teak lounge chairs
Exceptional
(53 reviews)

Cape Cod summer home on Slough Pond

Brewster

7% off
S$4,281
for 7 nights, 1 home
S$612 per night
includes taxes & fees
Cape Cod summer home on Slough Pond
Shuffle Board
Exceptional
(139 reviews)

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

Harwich

6% off
S$2,540
for 7 nights, 1 home
S$363 per night
includes taxes & fees
#Game Rm, ESPN, King Bds, Wi-Fi, Bikes,Beach Supplies, Quiet St, Central AC\Heat
Exterior
Wonderful
(23 reviews)

Charming antique Cape house

Harwich

8% off
S$3,263
for 7 nights, 1 home
S$466 per night
includes taxes & fees
Charming antique Cape house
Backyard with pool
Exceptional
(17 reviews)

3 homes in one, pool, outdoor kitchen, wk to beach, great for multiple families

Eastham

10% off
S$18,607
for 7 nights, 1 home
S$2,658 per night
includes taxes & fees
3 homes in one, pool, outdoor kitchen, wk to beach, great for multiple families
Deck with teak table and chairs
Exceptional
(97 reviews)

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

Chatham

7% off
S$4,826
for 7 nights, 1 home
S$689 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
0.1 miles to the private beach, a 3 minute walk
Exceptional
(9 reviews)

Modern beach house, steps to private beach, perfect for groups!

Eastham

7% off
S$4,213
for 7 nights, 1 home
S$602 per night
includes taxes & fees
Modern beach house, steps to private beach, perfect for groups!
Exterior
Exceptional
(7 reviews)

Newly Renovated Chatham Home overlooking Cranberry Bog.

West Chatham

7% off
S$6,638
for 7 nights, 1 home
S$948 per night
includes taxes & fees
Newly Renovated Chatham Home overlooking Cranberry Bog.
Not another house in sight
Exceptional
(36 reviews)

Your perch to the Cape's best ocean view with private Nauset access for 8!

Orleans

8% off
S$6,896
for 7 nights, 1 home
S$985 per night
includes taxes & fees
Your perch to the Cape's best ocean view with private Nauset access for 8!
Screened in back porch over looking landscaped yard
Exceptional
(32 reviews)

SECLUDED GEM IN THE VILLAGE - 2026 Calendar now posted

Wellfleet

20% off
S$2,632
for 7 nights, 1 home
S$376 per night
includes taxes & fees
SECLUDED GEM IN THE VILLAGE - 2026 Calendar now posted
Dusk in Chatham
Exceptional
(45 reviews)

Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!

South Chatham

8% off
S$5,263
for 7 nights, 1 home
S$752 per night
includes taxes & fees
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
View of steps from private deck off the bedrooms.
Exceptional
(80 reviews)

⭐️ STUNNING WATERFRONT ⭐️Pet Friendly 3BDRM/2BTH*FIREPIT*KAYAKS*GAS FIREPLACE*

Dennis

14% off
S$2,911
for 7 nights, 1 cottage
S$416 per night
includes taxes & fees
⭐️ STUNNING WATERFRONT ⭐️Pet Friendly 3BDRM/2BTH*FIREPIT*KAYAKS*GAS FIREPLACE*
Living area
Exceptional
(16 reviews)

Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball

Chatham

10% off
S$3,511
for 7 nights, 1 home
S$502 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Enjoy bug-free dining on brand new floor-to-ceiling screen porch & ceiling fan
Exceptional
(12 reviews)

Short Walk to Private Beach! Fully-Appointed House w New Screened Porch.

Brewster

8% off
S$5,894
for 7 nights, 1 home
S$842 per night
includes taxes & fees
Short Walk to Private Beach! Fully-Appointed House w New Screened Porch.
Outdoor dining
Exceptional
(58 reviews)

3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.

South Dennis

11% off
S$5,006
for 7 nights, 1 home
S$715 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
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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

Explore the beachside setting in Eastham

The beaches and forests provide a pleasant backdrop to your holiday home in Eastham. This city's seafood restaurants, hiking and cycling draw many visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Eastham

Are you hoping to find attractions to see during your stay? You'll be sure to enjoy Eastham for its hiking and cycling. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Eastham a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ocean Edge Golf Club (6.2 mi / 10 km)
  • Cranberry Valley Golf Course (10.3 mi / 16.6 km)
  • Cape Cod Lavender Farm (11 mi / 17.7 km)
  • Cape Cod Baseball & Bumper Boats (12.6 mi / 20.2 km)
  • Truro Vineyards of Cape Cod (14.8 mi / 23.9 km)
  • Cape Cod Inflatable Park (18.3 mi / 29.4 km)

Exploring the beaches and other natural features in Eastham

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Eastham is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Nauset Light Beach (1.5 mi / 2.4 km)
  • Nauset Beach (1.6 mi / 2.7 km)
  • First Encounter Beach (1.8 mi / 2.8 km)
  • Rock Harbor Beach (2.7 mi / 4.4 km)
  • Skaket Beach (3.2 mi / 5.2 km)
  • Marconi Beach (4.2 mi / 6.7 km)

Seasonal weather averages in Eastham

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

Travelling to and around Eastham

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 19.7 mi (31.6 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Provincetown, MA (PVC-Provincetown Municipal), which is 21.1 mi (34 km) away.

Frequently asked questions

What is the best area to stay in Eastham when booking a holiday rental?
One of the most popular neighbourhoods to find an Eastham holiday home is Campground Landing. When you lock in your holiday property, you can look forward to having the entire place to yourself. This means you won't have to share it with anybody apart from your group.
What is the most popular type of holiday rental accommodation in Eastham?
Houses are the most popular style of holiday rental in Eastham, according to our data. Even if you've got something a little different in mind, Vrbo has properties in all shapes and sizes. Take a look at our options to find your ideal fit.
How much does it cost to rent a holiday rental in Eastham?
A range of factors can influence what you'll pay for a holiday rental in Eastham, such as the season, length of stay and type of property. However, all of our holiday homes have one thing in common — incredible value. Just enter your travel dates to find your perfect match.
How much does it cost to rent a beach house in Eastham?
The average price for a holiday home by the beach in Eastham depends on when you're going and the size and style of property you're searching for. You can quickly and easily find prices on Vrbo by entering your dates of travel. Then use the filters to choose the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday rentals in Eastham?
Good news! Yes. You can pick from 110 holiday rentals that allow pets in Eastham. Plenty of our pet-friendly holiday rentals even come with a backyard for your fur child to play in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.
Can I rent a house with a pool in Eastham?
Add a new level of fun to your trip by booking your family into one of the 13 houses with a private pool in Eastham. Use our handy search filter to find the kind of property you want on Vrbo, and then spend lazy days splishing and splashing in a swimming pool that's for your exclusive use.
What are popular rental amenities in Eastham?
When it comes to rental amenities that people look for in Eastham, a garden, a water view and a fireplace rank the highest. With Vrbo holiday rentals, you'll enjoy choices to fit your taste and style, whether you're holidaying with friends, family or even pets.
Are there large group holiday rentals in Eastham?
Eastham has 16 holiday homes that can cater to 10 or more guests. These stays come with the privacy and space you need to enjoy good times with family and friends.
Are there holiday rentals in Eastham that welcome kids?
Bring the whole family together for an adventure in Eastham at one of our 110 family-friendly holiday properties. These stays offer conveniences that are just perfect for getaways with youngsters, such as kitchens, multiple bedrooms and pools. Simply click on the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Eastham?
Keeping the kiddos entertained during your holiday in Eastham is easy with these exciting family-friendly attractions:
  • Nauset Beach
  • Skaket Beach
  • Marconi Beach
Are there one-bedroom holiday rentals in Eastham?
There are 17 one-bedroom properties in Eastham to select from. A one-bedroom holiday rental is a wonderful choice if it's only you and your partner or if you're holidaying solo. Add in more space, convenience and privacy compared to a standard hotel, and you're bound to have a getaway to remember.
Can I find two-bedroom holiday rentals in Eastham?
Gather your family and relax in total privacy and comfort in one of the 33 two-bedroom holiday rentals Eastham has to offer.
Are there holiday rentals with WiFi in Eastham?
You can pick from 31 holiday rentals with WiFi in Eastham. If you want to disconnect from the world while on holiday, but still need to be connected to the web, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Eastham?
Decide on your travel dates and then make use of our filters to see holiday rentals with air conditioning in Eastham on Vrbo. With 98 air-conditioned properties to choose from here, you can enjoy a cool and comfy stay.
How old do you have to be to rent a holiday rental in Eastham?
The minimum required age is generally 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your preferred Eastham holiday home before booking your trip.
How long can I rent a holiday rental in Eastham for?
The amount of time you can rent an Eastham holiday home for differs depending on the property. Just put in your dates of travel to view options offering extended stays. They have everything you need to make your extended getaway more enjoyable and comfortable, such as kitchens and backyards. Some properties may also offer weekly or monthly discounts, so you can stay even longer for less.

More holiday ideas