Holiday Rentals in Wellfleet, MA

769 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Wellfleet, MA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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

Large House, For Multifamily, Pool, Walk To Beach - Wellfleet, MA
No reviews

Large House, For Multifamily, Pool, Walk To Beach

apartment, Eastham
This spacious Eastham property is situated 805 metres from Cooks Brook Beach, offering convenient access to the shore.
This five-bedroom dwelling accommodates ten guests and features a heated swimming pool, an outdoor kitchen with a pizza oven, and a coffee/wine bar, spread across four levels for ample living space.
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.
Charming Cottage With Association Pool - Delightful Coastal Retreat - Wellfleet, MA
No reviews

Charming Cottage With Association Pool - Delightful Coastal Retreat

house, Wellfleet
This cottage is situated on Route 6 in Wellfleet, a five-minute drive from Drummer Cove and 4.8 kilometres from Cshore Kitchen, offering convenient access to downtown Wellfleet's shops, Wellfleet Pier, and Mayo Beach.
This family-friendly holiday home accommodates up to six guests with three bedrooms and one bathroom, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, two decks, an enclosed outdoor shower, and access to a shared association swimming pool and laundry facility.
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.

Best Wellfleet, MA holiday rentals with a pool

Among the 769 accommodations in Wellfleet, MA, here are the 1 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.

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

Brand New Luxury 5 Bed Home - Wellfleet, MA
No reviews

Brand New Luxury 5 Bed Home

house, Eastham
This five-bedroom detached house is located in Eastham, 1.9 kilometres from Coast Guard Beach and 38.6 kilometres from Cape Cod Gateway Airport.
This detached house offers 358 square metres of living space with accommodation for up to 23 guests, featuring air conditioning, a fully equipped kitchen, private parking, a hot tub, and a sauna.
Tall Pines | House In Wellfleet - Wellfleet, MA
No reviews

Tall Pines | House In Wellfleet

apartment, Wellfleet
This Bohemian retreat is located in the pines of Wellfleet, adjacent to the historic Chequessett Burial Ground and First Meeting House (1723), and is a short 500-meter walk from Mayo Beach.
This 258 square meter flat, accommodating up to six guests, features three bedrooms and three bathrooms, a well-equipped kitchen, air conditioning, a terrace, and a separate ground-level living area, with the nearby Baker Field Recreation Area offering a playground and picnic facilities.

Best Wellfleet, MA holiday rentals with parking

Gorgeous Peaceful & Artistic Home! - Wellfleet, MA
9.7 44 reviews

Gorgeous Peaceful & Artistic Home!

apartment, Wellfleet
This contemporary Wellfleet house, near Wellfleet Bay and the National Seashore, is a short drive (approximately 2-3 km) from PB Boulangerie & Bistro and local beaches.
The four-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen with a new stove, a large private office, and a screened-in porch with swings; complete access to the entire house is provided.
Rock Lobster Bay Side Beach House - Wellfleet, MA
10 2 reviews

Rock Lobster Bay Side Beach House

apartment, Eastham
This Eastham apartment, situated on a quiet lane off Campground Road, is less than 0.8km from a private association beach and a public beach.
The two-bedroom, two-bathroom dwelling sleeps five, boasting a kitchen with fridge, microwave, and dishwasher, air conditioning, garden, parking, and easy access to Eastham's shops, restaurants, and Cape Cod attractions.
Charming Studio Cottage In Eastham! - Wellfleet, MA
9.0 94 reviews

Charming Studio Cottage In Eastham!

apartment, Eastham
This Wellfleet studio, situated in Eastham, lies approximately 32km south of Provincetown, near the Cape Cod National Seashore, 1.6km from the bay, and 2.4km from the beach.
The self-catering cottage, sleeping up to two guests, boasts a fully equipped kitchen, private deck overlooking woodland trails, and includes a new memory foam mattress, parking, and Wi-Fi; guests should note that linens are not provided.
Family Compound Walk To Downtown! - Wellfleet, MA
No reviews

Family Compound Walk To Downtown!

house, Wellfleet
This dog-friendly family compound in Wellfleet is a short walk to the town pier and village, and a 5-minute drive to ocean beaches.
This property offers three separate dwellings for up to 14 guests, featuring a private yard with space for games, a charcoal grill, and a ping pong table, alongside a main house with a great room and mini-split air conditioning throughout.
©2026 cozycozy.com