
Holiday rentals near Head of the Meadow Trail
We found 1,850 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals near Head of the Meadow Trail that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, such as parking and air conditioning. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Head of the Meadow Trail
Showing deals for:14 Nov - 21 Nov
Image gallery for Large House w/ample space- steps from Skaket Beach, close to CCRT and downtown!

1010 out of 10 rating
Exceptional
(8 reviews)
Large House w/ample space- steps from Skaket Beach, close to CCRT and downtown!
Orleans, MA
6% off
Price is NZ$15,108
NZ$15,108
NZ$2,158 per night
includes taxes & fees
Image gallery for Dream Beach House on Mayo Beach Wellfleet Cape Cod

1010 out of 10 rating
Exceptional
(16 reviews)
Dream Beach House on Mayo Beach Wellfleet Cape Cod
Wellfleet, MA
8% off
Price is NZ$20,849
NZ$20,849
NZ$2,978 per night
includes taxes & fees
Image gallery for Private Truro apt near Corn Hill Beach & Ptown, dog-friendly--laundry & parking!

1010 out of 10 rating
Exceptional
(11 reviews)
Private Truro apt near Corn Hill Beach & Ptown, dog-friendly--laundry & parking!
Truro, MA
7% off
Price is NZ$3,449
NZ$3,449
NZ$493 per night
includes taxes & fees
Image gallery for Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house

1010 out of 10 rating
Exceptional
(15 reviews)
Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house
Orleans, MA
8% off
Price is NZ$12,665
NZ$12,665
NZ$1,809 per night
includes taxes & fees
Image gallery for Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach

1010 out of 10 rating
Exceptional
(74 reviews)
Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach
Eastham, MA
7% off
Price is NZ$2,310
NZ$2,310
NZ$330 per night
includes taxes & fees
Image gallery for Oceanside OSLIL COTTAGE - Walk to Lecount Hollow Beach

9.89.8 out of 10 rating
Exceptional
(45 reviews)
Oceanside OSLIL COTTAGE - Walk to Lecount Hollow Beach
Wellfleet, MA
17% off
Price is NZ$7,015
NZ$7,015
NZ$1,002 per night
includes taxes & fees
Image gallery for Sun-filled, renovated house within minutes walk to private bay sides beach.

1010 out of 10 rating
Exceptional
(25 reviews)
Sun-filled, renovated house within minutes walk to private bay sides beach.
Eastham, MA
7% off
Price is NZ$5,297
NZ$5,297
NZ$757 per night
includes taxes & fees
Image gallery for Breathtaking Ocean Views

9.29.2 out of 10 rating
Wonderful
(29 reviews)
Breathtaking Ocean Views
North Truro, MA
16% off
Price is NZ$2,554
NZ$2,554
NZ$365 per night
includes taxes & fees
Image gallery for LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK

1010 out of 10 rating
Exceptional
(83 reviews)
LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK
North Truro, MA
7% off
Price is NZ$5,944
NZ$5,944
NZ$849 per night
includes taxes & fees
Image gallery for Cape Cod Pond Cottage

8.88.8 out of 10 rating
Excellent
(33 reviews)
Cape Cod Pond Cottage
Eastham, MA
8% off
Price is NZ$2,767
NZ$2,767
NZ$395 per night
includes taxes & fees
Image gallery for SECLUDED GEM IN THE VILLAGE - 2025 Calendar now posted

1010 out of 10 rating
Exceptional
(29 reviews)
SECLUDED GEM IN THE VILLAGE - 2025 Calendar now posted
Wellfleet, MA
21% off
Price is NZ$3,778
NZ$3,778
NZ$540 per night
includes taxes & fees
Image gallery for Clean and Quiet North Eastham Cottage Near Beaches

9.69.6 out of 10 rating
Exceptional
(20 reviews)
Clean and Quiet North Eastham Cottage Near Beaches
Eastham, MA
7% off
Price is NZ$3,789
NZ$3,789
NZ$541 per night
includes taxes & fees
Image gallery for Beautiful freestanding cottage on the beach. Privacy and beautiful sunsets.

1010 out of 10 rating
Exceptional
(13 reviews)
Beautiful freestanding cottage on the beach. Privacy and beautiful sunsets.
North Truro, MA
8% off
Price is NZ$5,432
NZ$5,432
NZ$776 per night
includes taxes & fees
Image gallery for Authentic Cape Cod Vacation Home

9.49.4 out of 10 rating
Exceptional
(6 reviews)
Authentic Cape Cod Vacation Home
Eastham, MA
7% off
Price is NZ$3,065
NZ$3,065
NZ$438 per night
includes taxes & fees
Image gallery for Large 4 Bed in prime location. A clean and comfortable home. 3 king, pkg.,yard

9.89.8 out of 10 rating
Exceptional
(29 reviews)
Large 4 Bed in prime location. A clean and comfortable home. 3 king, pkg.,yard
Provincetown, MA
8% off
Price is NZ$10,672
NZ$10,672
NZ$1,525 per night
includes taxes & fees
Image gallery for Don't Miss this Beachfront Gem!

9.69.6 out of 10 rating
Exceptional
(46 reviews)
Don't Miss this Beachfront Gem!
North Truro, MA
8% off
Price is NZ$4,356
NZ$4,356
NZ$622 per night
includes taxes & fees
Image gallery for Luxurious Beachfront 2 bedroom condo

1010 out of 10 rating
Exceptional
(19 reviews)
Luxurious Beachfront 2 bedroom condo
North Truro, MA
7% off
Price is NZ$4,320
NZ$4,320
NZ$617 per night
includes taxes & fees
Image gallery for SPACIOUS & PRIVATE 6 BEDRM HOME CLOSE TO THE OCEAN & BIKE PATH!

1010 out of 10 rating
Exceptional
(29 reviews)
SPACIOUS & PRIVATE 6 BEDRM HOME CLOSE TO THE OCEAN & BIKE PATH!
Eastham, MA
7% off
Price is NZ$6,547
NZ$6,547
NZ$935 per night
includes taxes & fees
Image gallery for Modern & Chic Oceanfront Beach Home in Historic N Truro

1010 out of 10 rating
Exceptional
(34 reviews)
Modern & Chic Oceanfront Beach Home in Historic N Truro
North Truro, MA
7% off
Price is NZ$3,406
NZ$3,406
NZ$487 per night
includes taxes & fees
Image gallery for Townhouse Beach Front Living - 2BD 3BA - Central AC - Linen Towels provided

1010 out of 10 rating
Exceptional
(34 reviews)
Townhouse Beach Front Living - 2BD 3BA - Central AC - Linen Towels provided
North Truro, MA
7% off
Price is NZ$4,806
NZ$4,806
NZ$687 per night
includes taxes & fees
Image gallery for Luxurious Entire Top Floor Condo 2 Fireplaces - 1200 sq ft, WIFI

9.89.8 out of 10 rating
Exceptional
(25 reviews)
Luxurious Entire Top Floor Condo 2 Fireplaces - 1200 sq ft, WIFI
Provincetown, MA
8% off
Price is NZ$6,261
NZ$6,261
NZ$894 per night
includes taxes & fees
Image gallery for Large and updated and condo, close to the center of town with 2 car parking!

1010 out of 10 rating
Exceptional
(31 reviews)
Large and updated and condo, close to the center of town with 2 car parking!
Provincetown, MA
7% off
Price is NZ$5,880
NZ$5,880
NZ$840 per night
includes taxes & fees
Image gallery for Luxury Waterfront, Gallery District, 2 BR, Private Deck, Parking, Central Air

1010 out of 10 rating
Exceptional
(108 reviews)
Luxury Waterfront, Gallery District, 2 BR, Private Deck, Parking, Central Air
Provincetown, MA
8% off
Price is NZ$5,509
NZ$5,509
NZ$787 per night
includes taxes & fees
Image gallery for One BR in perfect central Location on quiet st. King Bed, Private yard,w/d, Pkg.

9.69.6 out of 10 rating
Exceptional
(43 reviews)
One BR in perfect central Location on quiet st. King Bed, Private yard,w/d, Pkg.
Provincetown, MA
8% off
Price is NZ$3,318
NZ$3,318
NZ$474 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Head of the Meadow Trail
Modern Beachfront Condo, Gorgeous Views and Centrally Located
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Oceana Cottages
Sleeps 5 · 2 bedrooms
8.28.2 out of 10
Very goodvery good
57 reviews(57 reviews)
On The Beach! Relax and Unwind at your Private Waterfront Beach Bungalow
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
128 reviews(128 reviews)
Cozy waterfront studio w/direct beach access - close to town
Sleeps 4 · 1 bathroom
7.07.0 out of 10
Goodgood
39 reviews(39 reviews)
Immerse yourself in Ptown's vibrant heart at the center of Commercial Street
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Sandcastle Resort and Club
Sleeps 6 · 1 bedroom
7.47.4 out of 10
Goodgood
1,073 reviews(1,073 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value