Vacation Rentals with Pool in Head of the Meadow Trail, MA: Compare 10+ Sites & Save

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Massachusetts

  5.  North Truro
  6.  Head of the Meadow Trail

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38 Best Vacation Rentals with Pool in Head of the Meadow Trail (Starting from $139)

Horizons Beach Resort
Horizons Beach Resort
Apartment
North Truro, MA, USA
1.6k from Head of the Meadow Trail center

Fireplace/Heating, Pool, Oceanfront, Private Beach, Ocean View, Guest Services, View

58 Bedrooms37 Guests
8.8

Fabulous

31 reviews

$169
Average price / night
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Top Mast Resort-Anchor House, Private Beach Access.
Top Mast Resort-Anchor House, Private Beach Access.
Resort
North Truro, MA, 02652, United States
1.3k from Head of the Meadow Trail center

AC, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$628
Average price / night
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The Braemar Condominium
The Braemar Condominium
Apartment
Head of the Meadow Trail, North Truro, Massachusetts, USA
2.2k from Head of the Meadow Trail center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay

26 Bedrooms85 Guests
New to Booking
$219
Average price / night
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Top Mast Resort- Shore House! Beach, Pool, Housekeeping and more!
Top Mast Resort- Shore House! Beach, Pool, Housekeeping and more!
House
North Truro, MA, 02652, United States
1.3k from Head of the Meadow Trail center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

4 Bedrooms14 Guests
10.0

Exceptional

33 reviews

$429
Average price / night
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Sandcastle Resort
Sandcastle Resort
Apartment
Provincetown, MA, USA
2.8k from Head of the Meadow Trail center

Apartments, Accommodations, Pools, Parking, Serviced apartments, 3-star, Lodgings, Vacation rentals, Beach

33 Bedrooms48 Guests
7.3

Good

600 reviews

$139
Average price / night
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25x42 heated pool, pets, ADA, EV car charger, 4 ensuite, private beach
25x42 heated pool, pets, ADA, EV car charger, 4 ensuite, private beach
House
North Truro, MA, 02652, United States
2.2k from Head of the Meadow Trail center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms8 Guests
9.8

Exceptional

54 reviews

$1207
Average price / night
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Blue Cottage & Beach Condo
Blue Cottage & Beach Condo
Apartment
Provincetown, MA, USA
3.5k from Head of the Meadow Trail center

Apartments, Accommodations, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals, Condos

2 Bedrooms4 Guests
7.6

Good

5 reviews

$264
Average price / night
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North Truro  Condo W/Private Balcony and 2 Queen Beds
North Truro Condo W/Private Balcony and 2 Queen Beds
Condo
North Truro, MA, 02652, United States
2.2k from Head of the Meadow Trail center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

1 Bedroom4 Guests
9.8

Exceptional

36 reviews

$344
Average price / night
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The Blue Cottage
The Blue Cottage
Apartment
Provincetown, MA, USA
3.9k from Head of the Meadow Trail center

Balcony/Terrace, Fireplace/Heating, Pool, Security/Safety, Guest Services, View, Sports/Activities

1 Bedroom4 Guests
New to Booking
$506
Average price / night
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Modern East End Loft - Private Beach, In-Ground Pool Access, & Hot Tub!
Modern East End Loft - Private Beach, In-Ground Pool Access, & Hot Tub!
Condo
Provincetown, MA, 02657, United States
2.7k from Head of the Meadow Trail center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Microwave, No Smoking, Pool

1 Bedroom2 Guests
9.6

Exceptional

4 reviews

$307
Average price / night
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P-Town 2br Beach Beauty on the Bay. Water View!
P-Town 2br Beach Beauty on the Bay. Water View!
Apartment
Provincetown, MA, USA
3.9k from Head of the Meadow Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$165
Average price / night
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Provincetown Cottage: A/C, outdoor shower,parking,decks, pool, steps to beach.
Provincetown Cottage: A/C, outdoor shower,parking,decks, pool, steps to beach.
Cottage
Provincetown, MA, 02657, United States
2.7k from Head of the Meadow Trail center

AC, Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

2 Bedrooms2 Guests
9.8

Exceptional

33 reviews

$450
Average price / night
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Eastwood at Provincetown
Eastwood at Provincetown
Apartment
Provincetown, MA, USA
4.2k from Head of the Meadow Trail center

Apartments, Cheap, Accommodations, Pools, Parking, Serviced apartments, Romantic, Lodgings, Vacation rentals

11 Bedrooms6 Guests
8.6

Fabulous

682 reviews

$145
Average price / night
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Cozy condo on Commercial St. and close to Truro with pool and beach access!
Cozy condo on Commercial St. and close to Truro with pool and beach access!
Condo
Provincetown, MA, 02657, United States
2.9k from Head of the Meadow Trail center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

1 Bedroom3 Guests
7.6

Good

5 reviews

$365
Average price / night
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Beautiful backyard pool deeded beach rights
Beautiful backyard pool deeded beach rights
House
Truro, MA, USA
5.1k from Head of the Meadow Trail center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

4 Bedrooms8 Guests
New to Booking
$833
Average price / night
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Booking for SUMMER26! Heated pool, water views, hot tub , sauna, steam shower
Booking for SUMMER26! Heated pool, water views, hot tub , sauna, steam shower
House
Provincetown, MA, 02657, United States
3.1k from Head of the Meadow Trail center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

91 reviews

$868
Average price / night
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Brass Key Guesthouse Adults Only
Brass Key Guesthouse Adults Only
Resort
Provincetown, MA, USA
6.2k from Head of the Meadow Trail center

Cheap, Accommodations, Pools, Resorts, Parking, 4-star, Lodgings, Jacuzzis, Places to stay

37 Bedrooms16 Guests
9.3

Superb

101 reviews

$709
Average price / night
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Serene Waterfront Home with Heated Pool!
Serene Waterfront Home with Heated Pool!
House
Provincetown, MA, 02657, United States
3.2k from Head of the Meadow Trail center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
9.8

Exceptional

19 reviews

$2863
Average price / night
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Condo with Wading Pool Dog Welcome
Condo with Wading Pool Dog Welcome
House
Provincetown, MA, USA
6.4k from Head of the Meadow Trail center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

2 Bedrooms4 Guests
7.3

Good

8 reviews

$445
Average price / night
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Provincetown 2br Beach Beauty on the Bay Water View
Provincetown 2br Beach Beauty on the Bay Water View
Condo
Provincetown, MA, 02657, United States
3.9k from Head of the Meadow Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

16 reviews

$574
Average price / night
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Captivating Cottage
Captivating Cottage
Apartment
6.6k from Head of the Meadow Trail center

Apartments, Accommodations, Pools, Cottages, Lodgings, Hot tubs, Places to stay

1 Bedroom2 Guests
New to Booking
$264
Average price / night
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Sunny Cape Cod Poolside Haven (2407)
Sunny Cape Cod Poolside Haven (2407)
House
Truro, MA, 02652, United States
4.2k from Head of the Meadow Trail center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms9 Guests
9.4

Superb

3 reviews

$660
Average price / night
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Cottage with bonus living area in N. Truro, on the beautiful Outer Cape
Cottage with bonus living area in N. Truro, on the beautiful Outer Cape
Cottage
Truro, MA, 02659, United States
4.6k from Head of the Meadow Trail center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

26 reviews

$299
Average price / night
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Newly updated cozy condo, conveniently located near stunning beaches
Newly updated cozy condo, conveniently located near stunning beaches
Condo
North Truro, MA, 02652, United States
4.6k from Head of the Meadow Trail center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

15 reviews

$256
Average price / night
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3BD Contemporary--POOL! A/C, Deck & Walk to Great Hollow Beach
3BD Contemporary--POOL! A/C, Deck & Walk to Great Hollow Beach
House
Truro, MA, 02666, United States
6.0k from Head of the Meadow Trail center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$1730
Average price / night
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Luxury 3BR w/ Large Patio, Private Gym, Parking, Walk to Town, Dogs Welcome
Luxury 3BR w/ Large Patio, Private Gym, Parking, Walk to Town, Dogs Welcome
House
Provincetown, MA, 02657, United States
6.1k from Head of the Meadow Trail center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$1071
Average price / night
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Newly Updated Condo w/ Pool - Steps to Boatslip!
Newly Updated Condo w/ Pool - Steps to Boatslip!
Condo
Provincetown, MA, 02657, United States
6.4k from Head of the Meadow Trail center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

36 reviews

$571
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Head of the Meadow Trail.

Head of the Meadow Trail Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 38 verified vacation rentals with a pool in Head of the Meadow Trail. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Head of the Meadow Trail vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $139 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Head of the Meadow Trail offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Head of the Meadow Trail welcome pets. Currently, 8 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Head of the Meadow Trail often include additional outdoor features such as Pool, Fireplace/Heating, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Head of the Meadow Trail offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.