Holiday Rentals in Wellfleet, MA

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Wellfleet, MA holiday rentals
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769 Holiday rentals and Airbnb in Wellfleet, MA

Best family friendly Wellfleet, MA holiday rentals

Among the 769 accommodations in Wellfleet, MA, here are the 4 best family friendly rentals

Experience Cape Cod Beaches: Charming 4-bedroom Just A 10min Stroll To The Beach - Wellfleet, MA
9.5 50 reviews

Experience Cape Cod Beaches: Charming 4-bedroom Just A 10min Stroll To The Beach

apartment, Eastham
This family-friendly holiday home is located in Eastham, just 1.5km from Cape Cod Beaches and Campground Beach, with Arnold's Mini Golf and Thumpertown Beach also within 2km. It has excellent user, location and cleanliness ratings.
The property offers 141 square metres of space and can comfortably accommodate up to 8 guests. This well-equipped house has a fully fitted kitchen, a jacuzzi, a terrace, a garden, a spa, parking and air conditioning, plus free Wi-Fi and a barbecue for outdoor entertaining.
25-27% Off The Listed Price 2026  6 En-suite, Pets, Privacy, Views, Linens, Ada. - Wellfleet, MA
10 5 reviews

25-27% Off The Listed Price 2026 6 En-suite, Pets, Privacy, Views, Linens, Ada.

apartment, Truro
This 6-bedroom apartment in Truro is located 1.6 kilometres from Truro Vineyards of Cape Cod and Highland Golf Links, offering easy access to Cape Cod Beaches and Cape Cod National Seashore.
This spacious 232 square meter property accommodates up to 12 guests and includes a full kitchen, air conditioning, a terrace, a garden, and a private EV charger, with pets welcome and ADA accessibility.
Cape Cod Large Family Home Central  To Nauset Light Bike Trail And Bay Beaches - Wellfleet, MA
8.0 2 reviews

Cape Cod Large Family Home Central To Nauset Light Bike Trail And Bay Beaches

apartment, Eastham
This Eastham holiday home is situated near the Cape Cod National Seashore, a short drive from Nauset Light and Coast Guard Beaches, and conveniently located near the Cape Cod Rail Trail.
This three-bedroom, two-bathroom property sleeps six, offering a chef's kitchen, Wi-Fi, air conditioning, and a large lawn ideal for outdoor games; nearby attractions include the Wellfleet Drive-In and the Chequessett Golf Club.
Nature Lover's Nest - Wellfleet, MA
No reviews

Nature Lover's Nest

apartment, Wellfleet
This Wellfleet holiday home is situated a short drive (approx. 6.4 km) from the Cape Cod National Seashore and 4.8 km from Cape Cod beaches.
This four-bedroom, two-bathroom property sleeps nine guests and boasts a fully equipped kitchen with appliances including a dishwasher and lobster pot, laundry facilities, air conditioning, and barbecue grill; towels, hairdryer and linen are provided.

Best Wellfleet, MA holiday rentals with a pool

Among the 769 accommodations in Wellfleet, MA, here are the 4 best rentals with a pool

Cottage W Private Association Pool - Wellfleet, MA
9.0 1 review

Cottage W Private Association Pool

house, Wellfleet
This Wellfleet cottage is situated 2.6 km from Indian Neck Beach, 3.1 km from Wellfleet Bay Wildlife Sanctuary, and 5.3 km from Cape Cod National Seashore, offering easy access to local attractions.
This three-bedroom property, boasting 65 square metres of floor space and sleeping up to 11 guests, includes a fully equipped kitchen, private pool access, Wi-Fi, and a washing machine; nearby activities include nature walks and swimming.
Gorgeous Outdoor Areas With Heated Pool & Hot Tub! - Wellfleet, MA
9.8 8 reviews

Gorgeous Outdoor Areas With Heated Pool & Hot Tub!

house, Wellfleet
This luxurious Wellfleet residence is located within the Cape Cod National Seashore, offering proximity to Dyer Pond and a short drive to Great Pond, approximately 1.6 kilometres away.
This seven-bedroom, seven-bathroom property accommodates up to 16 guests, featuring a heated saltwater swimming pool, hot tub, game room with a pool table, ping-pong, and card tables, plus a newly renovated kitchen and split-system air conditioning.
Private Pool And Close To Marconi Beach! - Wellfleet, MA
9.7 34 reviews

Private Pool And Close To Marconi Beach!

apartment, Wellfleet
This spacious estate, located in the woods of Wellfleet, is a short bike ride from Marconi Beach and Lecount Hollow Beach, with easy access to the Cape Cod Rail Trail. The property comprises a main house and a separate guest house, offering 279 square metres of living space, four bedrooms, and a capacity of 12 guests, with amenities including a private pool, a well-equipped kitchen, and a dog-friendly policy.
Water Views Heated Pool & Hot Tub - Wellfleet, MA
No reviews

Water Views Heated Pool & Hot Tub

house, Wellfleet
This Wellfleet holiday home is situated a short walk (approximately 2.2 km) from the Wellfleet Bay Wildlife Sanctuary and a short drive from Mayo Beach and the Cape Cod National Seashore.
This eight-bedroom property boasts 618 square metres of floor space, sleeps 27 guests, includes a heated swimming pool, Jacuzzi, and a fully equipped kitchen, offering ample space and amenities for large groups.

Frequently asked questions about holiday rentals in Wellfleet, MA

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

    Wellfleet has a lot to offer! You can visit the Wellfleet Harbor, a beautiful spot to watch the sunset, or explore the Cape Cod National Seashore, which has miles of beaches and hiking trails. For a taste of history, head to the Wellfleet Historical Society Museum, which showcases the town's rich past.
  • What are the best Airbnb and holiday rentals in Wellfleet, MA?

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

    The paved bike path along the bay is a great option for a leisurely cycle, and it's perfect for all ages. If you're looking for a longer ride, the Cape Cod Rail Trail runs all the way from Dennis to Wellfleet, offering beautiful views of the countryside. For a scenic walk, try the trails at the Cape Cod National Seashore, particularly the ones leading to the Great Island National Wildlife Refuge.
  • What are the most popular Airbnbs in Wellfleet, MA?

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

    Wellfleet is a paradise for outdoor enthusiasts! You can enjoy swimming, sunbathing, and surfing at the many beaches, like Marconi Beach or Newcomb Hollow Beach. Kayaking and paddleboarding are also popular activities in the bay. For a more adventurous experience, try hiking or biking through the Cape Cod National Seashore.
  • What are the best holiday rentals with a pool in Wellfleet, MA?

    Rock On Wellfleet, Cozy Cottage - Bike Trail - Indoor Pool Access and Hatches Creek Sanctuary are the best holiday rentals with a pool in Wellfleet, MA.

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

    Wellfleet is conveniently located near other charming towns on Cape Cod. You can easily drive to Provincetown, known for its vibrant art scene and bustling waterfront. Truro, just north of Wellfleet, offers stunning beaches and a more tranquil atmosphere.
  • What are the best rentals for families and kids in Wellfleet, MA?

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

    Vacation rentals in Wellfleet usually come equipped with basic amenities like a kitchen, bathroom, and bedrooms. Many also offer extras like laundry facilities, Wi-Fi, and outdoor spaces such as decks or patios. Some rentals even have access to private beaches or swimming pools.
  • What are the best rentals or Airbnbs with a jacuzzi in Wellfleet, MA?

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

    The best time to visit Wellfleet depends on your preferences. Summer is the peak season with warm weather and plenty of sunshine, but it's also the busiest time. If you prefer a quieter experience, consider visiting during the shoulder seasons, spring or autumn, when the weather is still pleasant and the crowds are smaller.
  • What are the local dishes in Wellfleet, MA region?

    Wellfleet is famous for its fresh seafood, especially oysters. You can find them served raw, grilled, or in a variety of dishes. Another local favourite is the clam chowder, which is often served in a bread bowl. Don't forget to try the local lobster rolls, a classic Cape Cod delicacy.

Popular destinations

Best Wellfleet, MA holiday rentals with a balcony

Spacious And Modern Home, Close To Beach, Tom's Hill Private Setting. Home Ac - Wellfleet, MA
9.6 49 reviews

Spacious And Modern Home, Close To Beach, Tom's Hill Private Setting. Home Ac

apartment, Truro
This family-friendly holiday home is located just 1.6km from both Pamet River and Cape Cod Beaches, and within walking distance of Corn Hill Beach and the Truro Center for the Arts at Castle Hill, making it perfect for exploring Truro's cultural and natural attractions. The property has received excellent reviews from previous guests.
The 195 square metre home has three bedrooms and three bathrooms, comfortably accommodating up to six guests. The house features a fully equipped kitchen, a terrace, a garden, parking, a fireplace, and barbecue grills for outdoor dining, as well as free Wi-Fi for staying connected.
Shell City On Lt Island - Wellfleet, MA
9.6 7 reviews

Shell City On Lt Island

apartment, Wellfleet
This Wellfleet seaside property is a short walk (less than 2.4km) from Lieutenant Island and South Lieutenant Island Beach, and within 4.8km of Cape Cod National Seashore and White Cedar Swamp.
This 167 square metre house offers three bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, Wi-Fi, a patio, barbecue, and parking.
Pristine, Family-friendly Home W/ A Large Yard, Free Wifi, Private Washer/dryer - Wellfleet, MA
10 2 reviews

Pristine, Family-friendly Home W/ A Large Yard, Free Wifi, Private Washer/dryer

apartment, Eastham
This Eastham holiday home is located in a peaceful residential area, 2.4 kilometres from the nearest beach, with dining options along U.S. 6 and attractions such as Cape Cod National Seashore and First Encounter Beach within 5.6 kilometres.
This spacious, family-friendly apartment offers 163 square metres of living space, accommodating up to 7 guests across 3 bedrooms and 2 bathrooms, and features a well-equipped kitchen, air conditioning, a furnished deck, and a firepit.
Walk To Private Beach On Lt Island! - Wellfleet, MA
9.3 108 reviews

Walk To Private Beach On Lt Island!

apartment, Wellfleet
This five-bedroom house in South Wellfleet offers direct access to Lieutenant Island and Meadow Avenue Beach, with South Lieutenant Island Beach and Cape Cod National Seashore within a 5km radius.
The 297 square metre property has a garden, terrace, barbecue facilities and parking, comfortably accommodating up to 11 guests.

Best Wellfleet, MA holiday rentals with parking

Gardens And Yard W/ Playset; Near Paths To Ponds! - Wellfleet, MA
10 61 reviews

Gardens And Yard W/ Playset; Near Paths To Ponds!

apartment, Wellfleet
This Wellfleet cottage, a former schoolhouse dating from 1900-1938, is situated on Route 6, less than 1.6km from the town centre and within 1.6km of the Rail Trail, Dyer Pond, and Duck Pond.
Sleeping four guests, this two-bedroom, one-bathroom property boasts a kitchen with dishwasher, air conditioning, a private garden with a deck, Weber grill, and playset, plus a dedicated office space; nearby activities include exploring the Wellfleet Bay Wildlife Sanctuary.
Wellfleet Oasis - Wellfleet, MA
10 67 reviews

Wellfleet Oasis

house, Wellfleet
This Wellfleet studio apartment is conveniently located near the Massachusetts Audubon Society's Wellfleet Bay Wildlife Sanctuary and 2.1 km from Marconi Beach, accessible via a nearby cycle path.
The self-contained unit sleeps two, features a modern design with a private deck, Ninja Grill, fully equipped kitchenette with induction hob, and all-tile shower; owners are on-site for assistance.
Shell City~walk To Beach/dog Friendly/kayaks - Wellfleet, MA
9.7 32 reviews

Shell City~walk To Beach/dog Friendly/kayaks

apartment, Wellfleet
Lieutenant's Island, Wellfleet, Massachusetts offers a dog-friendly (one dog, over 1 year, fee applies) three-bedroom house, easily accessible via a causeway, close to Wellfleet Bay Wildlife Sanctuary and beaches.
This spacious, newly renovated property sleeps up to 11 guests, boasting a gourmet kitchen, wraparound deck, kayaks, bikes, gas grill, Roku TVs, washer/dryer, outside shower, and an award-winning digital house guide; enjoy shell-laden road access (subject to tides), proximity to Loagy Bay for shell and horseshoe crab hunting.
Wellfleet Woods Escape - Wellfleet, MA
9.8 213 reviews

Wellfleet Woods Escape

apartment, Wellfleet
This charming holiday home is located just a short distance from Wellfleet's beautiful bay, offering a peaceful retreat in a wooded setting. The property has been highly rated by previous guests, with excellent scores for location, cleanliness, and overall experience.
The property has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the modern kitchen, complete with a dishwasher, and relax in the open living area with its wood-beamed ceiling, or step outside to the garden and enjoy the outdoor shower and stunning bay views.
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