Holiday Rentals in Eastham, MA

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Eastham, MA holiday rentals
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Best Holiday rentals and Airbnb offers in Eastham, MA

Best family friendly Eastham, MA holiday rentals

Among the 794 accommodations in Eastham, MA, here are the 4 best family friendly rentals

New 2026 Charming Home Just Over A Mile To Coast G - Eastham, MA
Eastham, MA
18/07 – 25/07
SG$951/nighttotal: SG$6657 (7 )

New 2026 Charming Home Just Over A Mile To Coast G

1 4
apartment , Eastham
This Eastham holiday let offers a prime location, a short walk from the Cape Cod National Seashore visitor centre and approximately 2.4 kilometres from Coast Guard Beach.
This family-friendly holiday home accommodates eight guests across four bedrooms and features two bathrooms, air conditioning, a garden, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Walk To Beach/kayaks/bocce/bay Cottage - Eastham, MA
9.7 62 reviews
Eastham, MA
12/09 – 10/10
SG$278/nighttotal: SG$7784 (28 )

Walk To Beach/kayaks/bocce/bay Cottage

2 2
apartment , Eastham
This charming cottage is located in Thumpertown, Eastham, just a 200-metre walk from the beach and a short drive from Wiley Park and Great Pond. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The two-bedroom holiday home comfortably sleeps up to four guests and features a sunroom with a trundle bed, a fully equipped kitchen, and a bathroom. Guests can enjoy complimentary kayaks, a patio with a BBQ area, a bocce court, and a lush vegetable garden, along with a guide offering local tips and recommendations.
Waterfront Just Discounted - September 2025 Discounted 25% - Book Today - Eastham, MA
9.4 63 reviews
Eastham, MA
18/07 – 25/07
SG$1473/nighttotal: SG$10311 (7 )

Waterfront Just Discounted - September 2025 Discounted 25% - Book Today

4 4
apartment , Eastham
This four-bedroom, three-bathroom property is situated in Eastham, just a short drive from whale watching trips in Hyannis or Provincetown.
The 186 square metre house boasts a spacious living area, a modern kitchen with granite countertops, a large deck with a fire pit, and a private garden, comfortably accommodating up to seven guests.
Condo ∙ 2 Bedrooms ∙ 6 Guests - Eastham, MA
Eastham, MA
27/06 – 04/07
SG$639/nighttotal: SG$4473 (7 )

Condo ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Brewster
This two-bedroom townhouse, situated within the Ocean Edge Resort in Howland Village, Brewster, offers convenient access to Route 6A/Main Street and Route 137.
The property boasts a spacious layout including a loft with a queen-size sofa bed, accommodating up to six guests, and features a fully equipped kitchen, washer/dryer, Wi-Fi, Apple TV, and a patio with grill; plus optional access to the Ocean Edge Resort pool.

Best Eastham, MA holiday rentals with a pool

Among the 794 accommodations in Eastham, MA, here are the 4 best rentals with a pool

Private Pool 3 Mins To Skaket Beach! - Eastham, MA
9.5 50 reviews
Eastham, MA
15/08 – 22/08
SG$2414/nighttotal: SG$16898 (7 )

Private Pool 3 Mins To Skaket Beach!

4 7
apartment , Orleans
This holiday home is situated in Orleans, just 2 kilometres from Cape Cod Beaches, Skaket Beach, and the Church of the Transfiguration. The property enjoys excellent user, location, and cleanliness ratings. This spacious 307 square metre property has four bedrooms and can accommodate up to 10 guests. The house offers a private pool, a garden, a barbecue grill, and a balcony for outdoor enjoyment, as well as modern amenities including a washing machine, a dishwasher, and a microwave.
108 M² House ∙ 2 Bedrooms ∙ 6 Guests - Eastham, MA
Eastham, MA
27/06 – 04/07
SG$618/nighttotal: SG$4326 (7 )

108 M² House ∙ 2 Bedrooms ∙ 6 Guests

2 2
house , Brewster
This Cape Cod property is located within the Ocean Edge Villages in Brewster, a short drive from Main Street and local beaches.
This 108 square meter, 2-bedroom, 2-bathroom holiday home accommodates up to 6 guests and offers a swimming pool, tennis court, garden, and parking, with optional passes for resort amenities and included daily activities such as golf and bike rentals.
Private Pool 3 Mins To Skaket Beach - Eastham, MA
Eastham, MA
12/09 – 10/10
SG$827/nighttotal: SG$23156 (28 )

Private Pool 3 Mins To Skaket Beach

4 2
house , Orleans
This Orleans holiday home is situated a 1.2km walk or a 2.4km drive from Skaket Beach, close to Dyer Prince Beach (1.8km away), offering easy access to other Cape Cod attractions.
This four-bedroom, three-bathroom property boasts a 307 square metre floor area, accommodating up to 19 guests and featuring a private pool, fully equipped kitchen with dishwasher, free Wi-Fi, cable TV, washing machine, fireplace, and parking.
108 M² Condo ∙ 2 Bedrooms ∙ 6 Guests - Eastham, MA
Eastham, MA
27/06 – 04/07
SG$673/nighttotal: SG$4711 (7 )

108 M² Condo ∙ 2 Bedrooms ∙ 6 Guests

2 2
apartment , Brewster
This two-bedroom, two-bathroom flat is located in the Ocean Edge Resort area of Brewster, offering easy access to Martha's Vineyard and Nantucket via ferry.
Guests can enjoy complimentary weekly activities valued up to £490, including daily tickets for golf, bike or kayak hire, whale watching cruises, and round-trip ferry tickets, with optional access to Arbor and Fletcher Pools, Fletcher Cardio Centre, and children's activities for a fee.

Frequently asked questions about holiday rentals in Eastham, MA

  • What are some interesting places to visit in or near Eastham, MA?

    Eastham is a great place to visit for nature lovers. You can visit the Cape Cod National Seashore, a beautiful stretch of coastline with beaches, dunes, and forests. You can also visit the Nauset Light, a historic lighthouse that offers stunning views of the Atlantic Ocean. There are also plenty of other things to see and do in Eastham, including visiting the Eastham Windmill, exploring the Cape Cod Rail Trail, and taking a ferry to the nearby islands.
  • What are the best Airbnb and vacation rentals in Eastham, MA?

  • Which walking or cycling routes are the best in Eastham, MA?

    The Cape Cod Rail Trail is a popular choice for walking and cycling. It's a paved, 35-kilometre-long trail that runs through Eastham and several other towns on Cape Cod. The trail is flat and easy to navigate, making it a great option for families with young children. There are also a number of shorter walking trails in Eastham, including the Nauset Marsh Trail and the Coast Guard Beach Trail.
  • What are the most popular Airbnbs in Eastham, MA?

    Among the Airbnbs in Eastham, MA, Cute Cottage Living By The Sea, Cape Cod Suite Near Private Beach and Eastham Escape are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Eastham, MA?

    Eastham is a great place to enjoy outdoor activities. You can go swimming, sunbathing, and surfing at the beaches. You can also go kayaking, paddleboarding, and windsurfing in the bay. If you like hiking, there are many trails to explore in the Cape Cod National Seashore. You can also go birdwatching, fishing, and whale watching in the area.
  • What are the best vacation rentals with a pool in Eastham, MA?

  • What other towns or cities can be easily accessed from Eastham, MA?

    Eastham is well-connected to other towns and cities on Cape Cod. You can easily drive to nearby towns like Wellfleet, Truro, and Orleans. You can also take the Cape Cod Regional Transit Authority bus to other towns and cities on the Cape. If you want to explore further afield, you can take a ferry to Nantucket or Martha's Vineyard.
  • What are the best rentals for families and kids in Eastham, MA?

  • What amenities are commonly available in vacation rentals in Eastham, MA?

    Vacation rentals in Eastham typically have a range of amenities, depending on the property. Common amenities include a kitchen, bathroom, bedrooms, living room, and outdoor space. Some vacation rentals may also have amenities like a swimming pool, hot tub, or fireplace. You can find vacation rentals with different levels of luxury and amenities to suit your needs and budget.
  • What are the best rentals or Airbnbs with a jacuzzi in Eastham, MA?

  • What time of year is best to rent a vacation rental Eastham, MA?

    The best time to rent a vacation rental in Eastham depends on your preferences. Summer is the most popular time to visit, but it can be crowded and expensive. If you're looking for a more relaxed experience, consider visiting in the spring or autumn. The weather is still pleasant during these seasons, and the crowds are smaller. You can find some great deals on vacation rentals during the off-season.

Destinations nearby

Best Eastham, MA holiday rentals with a balcony

Chic Boho Escape Minutes To Nauset Beach! - Eastham, MA
Eastham, MA
18/07 – 25/07
SG$1113/nighttotal: SG$7791 (7 )

Chic Boho Escape Minutes To Nauset Beach!

4 4
apartment , Orleans
This stylish, boho-inspired apartment in East Orleans is located just 2.4 kilometres from Nauset Beach and a short drive from Skaket Beach and downtown Orleans.
With 121 square metres of living space, this property offers four bedrooms, three bathrooms, accommodates up to eight guests, and features a fully equipped kitchen, a game room, a backyard with various activities, and an outdoor firepit.
Four Season Modern Cape Cod Cottage (With Heat) - Eastham, MA
9.7 14 reviews
Eastham, MA
15/08 – 22/08
SG$891/nighttotal: SG$6237 (7 )

Four Season Modern Cape Cod Cottage (With Heat)

2 2
house , Eastham
This two-bedroom cottage is situated in Eastham's Historic Town Center, just a short walk from Salt Pond and the National Seashore Visitor Centre.
The 53 square metre property features a fully equipped kitchen, a private garden, and parking for two vehicles, making it ideal for families or small groups looking for a comfortable and convenient base to explore the Cape Cod peninsula.
Seaside Retreat W/ Private Beach Landing! - Eastham, MA
9.6 127 reviews
Eastham, MA
15/08 – 22/08
SG$1116/nighttotal: SG$7812 (7 )

Seaside Retreat W/ Private Beach Landing!

3 2
apartment , Eastham
This waterfront holiday home in Eastham is ideally situated just 2 kilometres from the Edward Penniman House and Barn, Eastham Windmill, and Jonathan Young Windmill, making it a great base for exploring this historic area of Cape Cod. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The house is spread across 78 square metres and comfortably accommodates up to 6 guests in its 3 bedrooms and 1 bathroom. Guests can enjoy a range of amenities, including a private spa tub, fireplace, gas grills, and a fully equipped kitchen, as well as direct access to the water for fishing, kayaking, or simply relaxing by the shore.
Updated Waterfront Gem On Saltwater Town Cove W/ Private Dock & Sunrise Views - Eastham, MA
9.6 38 reviews
Eastham, MA
12/09 – 10/10
SG$1152/nighttotal: SG$32256 (28 )

Updated Waterfront Gem On Saltwater Town Cove W/ Private Dock & Sunrise Views

3 2
apartment , Eastham
This Eastham waterside residence provides direct access to Saltwater Town Cove, with the Cape Cod National Seashore beaches 4 kilometres away and Orleans eateries just over 1 kilometre distant.
This 158 square metre holiday home, accommodating up to six guests, features three bedrooms, two bathrooms, a newly remodelled open-concept living area, two distinct living rooms, and a private driveway for three cars, with kayaking and paddleboarding opportunities readily available.

Best Eastham, MA holiday rentals with parking

Modern Contempory With Views Of Cape Cod Bay - Eastham, MA
Eastham, MA
18/07 – 25/07
SG$1155/nighttotal: SG$8085 (7 )

Modern Contempory With Views Of Cape Cod Bay

2 4
apartment , Eastham
This Eastham holiday let is located just 800 metres from South Sunken Meadow Beach and boasts views of Cape Cod Bay.
This newly remodelled, contemporary two-bedroom flat accommodates up to four guests and features expansive decking, a modern kitchen with a dishwasher, and is ideally situated for exploring the Cape Cod National Seashore, cycling, and kayaking.
Beach & Town Walkable:family Friendly Cape Getaway - Eastham, MA
9.6 17 reviews
Eastham, MA
15/08 – 22/08
SG$1891/nighttotal: SG$13237 (7 )

Beach & Town Walkable:family Friendly Cape Getaway

4 7
apartment , Eastham
This Eastham holiday home is situated within 3.2km of Campground Beach and Thumpertown Beach, offering easy access to Cape Cod's coastline.
The four-bedroom, four-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private balcony, garden, free Wi-Fi, and parking; limited housekeeping is provided.
Welcome To Wellfleet! Classically Modern, Woodsy And Serene. - Eastham, MA
9.6 8 reviews
Eastham, MA
18/07 – 25/07
SG$547/nighttotal: SG$3829 (7 )

Welcome To Wellfleet! Classically Modern, Woodsy And Serene.

2 4
cottage , Wellfleet
This cottage is located in South Wellfleet, a mere 1-minute drive from the Cape Cod National Seashore and 3 minutes from local beaches.
This 72 square meter holiday home sleeps four guests in two bedrooms, offering a private terrace with barbecue facilities, Wi-Fi, and air conditioning, with attractions like Uncle Tim's Bridge and Cape Cod Beaches within easy reach.
Lovely Home Close To Bike Bath And Beach - Eastham, MA
9.0 1 review
Eastham, MA
18/07 – 25/07
SG$1082/nighttotal: SG$7574 (7 )

Lovely Home Close To Bike Bath And Beach

3 4
house , Eastham
This Eastham holiday home is conveniently located a short walk from Herring Brook Beach and within an 8-11 km radius of Nauset Lighthouse, Wellfleet Bay Wildlife Sanctuary, and Cape Cod National Seashore.
This 153 square metre property boasts three bedrooms, two bathrooms, sleeps seventeen guests, and includes a fully equipped kitchen, private garden, free Wi-Fi, and in-house laundry facilities.
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