Eastham holiday rentals

We found 2,635 holiday rentals — enter your dates for availability
Select from 296 homes, 73 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:13 Nov - 20 Nov

Private kitchen
Exterior
Outdoor dining
Living area
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
S$1,024
for 7 nights, 1 cottage
S$146 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Full view of backyard with in ground pool
Backyard view of house
Large family room with lots of seating; perfect for family game night
Dining room, looking into home office
Exceptional
(29 reviews)

Immaculately maintained, large beach home with heated swimming pool

Eastham

8% off
S$7,516
for 7 nights, 1 home
S$1,074 per night
includes taxes & fees
Immaculately maintained, large beach home with heated swimming pool
New Chefs Kitchen
Breakfast Nook with Pool View
Second Deck Bar Sitting/Dining Area
Garden Entrance
Exceptional
(35 reviews)

Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes

Brewster

7% off
S$6,538
for 7 nights, 1 home
S$934 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
Living area
Pool
Living area
Kitchen
Exceptional
(68 reviews)

Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!

Orleans

8% off
S$15,908
for 7 nights, 1 home
S$2,273 per night
includes taxes & fees
Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!
Living room
Private beach/dock area
View of property
Downstairs bedroom
Exceptional
(18 reviews)

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

South Chatham

8% off
S$9,254
for 7 nights, 1 home
S$1,322 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Hot tub spa
Eat-in kitchen with oversized island is great for entertaining
Mudroom and laundry
Primary bedroom (king bed)
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

7% off
S$8,109
for 7 nights, 1 home
S$1,158 per night
includes taxes & fees
Family friendly luxury home with heated pool and spa
Fabulous family room, a magnet for family gatherings
Deeded access to nearby Mill Pond to launch your Kayak
Well equipped chef's kitchen w. stainless steel appliances
Light & bright second floor great room
Exceptional
(119 reviews)

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

Chatham

25% off
S$6,775
for 7 nights, 1 home
S$968 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Refreshing outdoor shower
Wet bar in the pool room
Game room with beautiful pool table and wet bar.
two-story entrance Foyer
Exceptional
(24 reviews)

Spacious home - Sleeps 15 -Steps to a Private Beach

Dennis

7% off
S$11,099
for 7 nights, 1 home
S$1,586 per night
includes taxes & fees
Spacious home - Sleeps 15 -Steps to a Private Beach
Interior
Exterior
rear view of house
Private kitchen
Exceptional
(58 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
S$10,205
for 7 nights, 1 home
S$1,458 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Master Bedroom - King Bed, TV, Bureau and ensuite bath
Shuffle Board
Living Room
Kitchen, Dining area:  Fridge, Stove, Dishwasher
Exceptional
(137 reviews)

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

Harwich

6% off
S$2,898
for 7 nights, 1 home
S$414 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Lower level living room
Property grounds
Dining room
Pottery Barn teak lounge chairs
Exceptional
(50 reviews)

Cape Cod summer home on Slough Pond

Brewster

7% off
S$4,267
for 7 nights, 1 home
S$610 per night
includes taxes & fees
Cape Cod summer home on Slough Pond
Exterior
Marina
Interior
Outdoor dining
Exceptional
(43 reviews)

Rates just lowered for last week of July and Aug with 5 night min accepted.

South Dennis

7% off
S$1,753
for 7 nights, 1 home
S$250 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Kitchen with island
Deck with teak table and chairs
Living room with cathedral ceiling - open floor plan
Interior
Exceptional
(90 reviews)

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

Chatham

7% off
S$4,863
for 7 nights, 1 home
S$695 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
2000+ SF multi level patio, pool, pool house, outdoor kitchen, fire pit & more!
Center island with seating for 4
Front Den looking in to kitchen
Fire pit & couch
Exceptional
(43 reviews)

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham

8% off
S$12,296
for 7 nights, 1 home
S$1,757 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
The Woolrych House sits above a private Brewster beach.
Outdoor dining
Upstairs queen in View Room
View from second floor.
Exceptional
(50 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
S$6,207
for 7 nights, 1 home
S$887 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Master bedroom upstairs with TV.
Upstairs master bedroom
Kitchen
Front Door
Exceptional
(105 reviews)

Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area

West Chatham

7% off
S$2,660
for 7 nights, 1 home
S$380 per night
includes taxes & fees
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
Seating for 3 at kitchen counter
Outdoor dining
Updated Kitchen for Summer 2020
Fully equipped
Dining
Exceptional
(55 reviews)

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

South Dennis

12% off
S$4,888
for 7 nights, 1 home
S$698 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Private kitchen
Living area
Property grounds
Room
Exceptional
(15 reviews)

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

Chatham

10% off
S$4,199
for 7 nights, 1 home
S$600 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Like being on a cruise ship!
Propane fire-pit for cool nights. Evening view.
Charming & cozy.
Large LR w/ wood burning fireplace, Samsung Frame TV &expansive picture window.
Exceptional
(28 reviews)

★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets

Brewster

7% off
S$6,088
for 7 nights, 1 home
S$870 per night
includes taxes & fees
★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
Living area
Private kitchen
Interior
Exterior
Exceptional
(10 reviews)

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

Dennis

7% off
S$3,820
for 7 nights, 1 home
S$546 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Living room looking toward front
Living room looking toward front / first floor front bedroom door
Kitchen
Second floor front bedroom with view of Cape Cod Bay
Exceptional
(28 reviews)

Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!

Eastham

6% off
S$4,613
for 7 nights, 1 home
S$659 per night
includes taxes & fees
Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!
Room
Outdoor dining
Dining
Living area
Exceptional
(29 reviews)

Sun-filled, renovated house within minutes walk to private bay sides beach.

Eastham

7% off
S$4,370
for 7 nights, 1 home
S$624 per night
includes taxes & fees
Sun-filled, renovated house within minutes walk to private bay sides beach.
TV viewing area with queen sleeper sofa in loft
Loft living room
Modern cape architecture
King bed in primary suite
Exceptional
(6 reviews)

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

Eastham

10% off
S$4,041
for 7 nights, 1 home
S$577 per night
includes taxes & fees
Modern beach house, steps to private beach, perfect for groups!
Private kitchen
The Chatham downtown is filled with cute shops and restaurants.
Living area
Room
Exceptional
(6 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

7% off
S$4,944
for 7 nights, 1 home
S$706 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
  • 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

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)
  • 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)
  • Commercial Street (18.7 mi / 30 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:

  • Cape Cod Beaches (10.5 mi / 16.9 km)
  • Nauset Light Beach (1.5 mi / 2.4 km)
  • Nauset Beach (1.6 mi / 2.7 km)
  • Skaket Beach (3.2 mi / 5.2 km)
  • Marconi Beach (4.2 mi / 6.7 km)
  • Breakwater Beach (7.1 mi / 11.4 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