Oceanfront Rentals in Academy Playhouse, MA: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
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  4.  Massachusetts

  5.  Orleans
  6.  Academy Playhouse

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692 Best Oceanfront Rentals in Academy Playhouse (Starting from $257)

Orleans Holiday House
Orleans Holiday House
House
Orleans, MA, USA
1.4k from Academy Playhouse center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay, Family

5 Bedrooms8 Guests
New to Booking
$262
Average price / night
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4 miles to Orleans beaches & close to town!
4 miles to Orleans beaches & close to town!
House
Orleans, MA, 02653, United States
0.1k from Academy Playhouse center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
9.8

Exceptional

22 reviews

$2317
Average price / night
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Salty Ridge Station
Salty Ridge Station
House
Orleans, MA, USA
2.1k from Academy Playhouse center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$632
Average price / night
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Walk to Town, Fully Renovated!
Walk to Town, Fully Renovated!
Apartment
Orleans, MA, 02653, United States
0.3k from Academy Playhouse center

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

6 Bedrooms12 Guests
9.4

Superb

3 reviews

$811
Average price / night
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Areys Pond Point
Areys Pond Point
House
Orleans, MA, USA
2.5k from Academy Playhouse center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

4 Bedrooms8 Guests
8.0

Good

1 reviews

$394
Average price / night
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Stylish Orleans home with spacious deck - near bay & ocean beach
Stylish Orleans home with spacious deck - near bay & ocean beach
House
Orleans, MA, 02653, United States
0.5k from Academy Playhouse center

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

4 Bedrooms8 Guests
8.4

Very Good

40 reviews

$306
Average price / night
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Walk to Skaket Beach Charming Cottage with Deck
Walk to Skaket Beach Charming Cottage with Deck
House
Orleans, MA, USA
2.6k from Academy Playhouse center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$629
Average price / night
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Town Cove Coastal Chic
Town Cove Coastal Chic
House
Orleans, MA, 02653, United States
0.7k from Academy Playhouse center

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

3 Bedrooms6 Guests
New to Booking
$845
Average price / night
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Namskaket Retreat
Namskaket Retreat
House
Orleans, MA, USA
2.7k from Academy Playhouse center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

3 Bedrooms6 Guests
9.0

Fabulous

1 reviews

$619
Average price / night
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Walk to Water, Cozy, Dog Friendly!
Walk to Water, Cozy, Dog Friendly!
House
Orleans, MA, 02653, United States
0.7k from Academy Playhouse center

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

3 Bedrooms8 Guests
New to Booking
$482
Average price / night
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Island Bay Bungalow
Island Bay Bungalow
House
Eastham, MA, USA
3.0k from Academy Playhouse center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Bungalows

3 Bedrooms6 Guests
8.5

Very Good

2 reviews

$257
Average price / night
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Coastal Chic sunny and private in East Orleans \"center\" w  bed/bath rebuild 2024
Coastal Chic sunny and private in East Orleans \"center\" w bed/bath rebuild 2024
House
Orleans, MA, 02653, United States
0.7k from Academy Playhouse center

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

3 Bedrooms6 Guests
9.8

Exceptional

30 reviews

$560
Average price / night
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2 Bed 1 Bath Vacation home in Eastham
2 Bed 1 Bath Vacation home in Eastham
House
Eastham, MA, USA
4.8k from Academy Playhouse center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms4 Guests
9.7

Exceptional

3 reviews

$321
Average price / night
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Sprawling Home With Private Association Lake Access (2289)
Sprawling Home With Private Association Lake Access (2289)
House
Orleans, MA, 02653, United States
0.7k from Academy Playhouse center

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

5 Bedrooms11 Guests
9.0

Fabulous

6 reviews

$925
Average price / night
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Cape Landing Cottage
Cape Landing Cottage
House
Brewster, MA, USA
4.8k from Academy Playhouse center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$660
Average price / night
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Family Tides home, perfect for up to 10 guests.
Family Tides home, perfect for up to 10 guests.
House
Orleans, MA, 02653, United States
0.8k from Academy Playhouse center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

5 Bedrooms10 Guests
9.4

Superb

6 reviews

$1108
Average price / night
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6 Mi to Beach Home with Deck in Brewster!
6 Mi to Beach Home with Deck in Brewster!
House
Brewster, MA, USA
4.9k from Academy Playhouse center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$294
Average price / night
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Orleans Dreams: 013-OP  Luxurious 5-Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water!
Orleans Dreams: 013-OP Luxurious 5-Bedroom Retreat with Heated Pool & Hot Tub – Walk to Water!
House
Orleans, MA, 02653, United States
0.8k from Academy Playhouse center

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

5 Bedrooms12 Guests
New to Booking
$1450
Average price / night
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Lookout at Pleasant Bay with a private beach
Lookout at Pleasant Bay with a private beach
House
Orleans, MA, USA
5.3k from Academy Playhouse center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay, Family

3 Bedrooms8 Guests
New to Booking
$421
Average price / night
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Second Wind :039-O  An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24
Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24
House
Orleans, MA, 02653, United States
0.8k from Academy Playhouse center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

10 Bedrooms24 Guests
10.0

Exceptional

14 reviews

$3170
Average price / night
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Central AC Close to Nauset Beach!
Central AC Close to Nauset Beach!
House
Orleans, MA, 02653, United States
0.8k from Academy Playhouse center

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

4 Bedrooms10 Guests
10.0

Exceptional

13 reviews

$595
Average price / night
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Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
Condo
Orleans, MA, 02653, United States
0.8k from Academy Playhouse center

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

2 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$297
Average price / night
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Sweeping Water Views, Walk to Town, Outdoor Shower!
Sweeping Water Views, Walk to Town, Outdoor Shower!
House
Orleans, MA, 02657, United States
0.9k from Academy Playhouse center

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

3 Bedrooms6 Guests
New to Booking
$557
Average price / night
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Waterfront on Crystal Lake!
Waterfront on Crystal Lake!
House
Orleans, MA, 02653, United States
0.9k from Academy Playhouse center

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

3 Bedrooms6 Guests
9.8

Exceptional

29 reviews

$721
Average price / night
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Waterfront on the Cove, NEW Kitchen and Central AC
Waterfront on the Cove, NEW Kitchen and Central AC
House
Orleans, MA, 02653, United States
0.9k from Academy Playhouse center

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

3 Bedrooms7 Guests
9.8

Exceptional

14 reviews

$662
Average price / night
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Recently Renovated Home Close to Nauset Beach and Downtown Orleans (2326)
Recently Renovated Home Close to Nauset Beach and Downtown Orleans (2326)
House
Orleans, MA, 02653, United States
1.0k from Academy Playhouse center

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

3 Bedrooms6 Guests
7.6

Good

5 reviews

$472
Average price / night
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4 Bedroom Meetinghouse Pond Waterfront
4 Bedroom Meetinghouse Pond Waterfront
House
Orleans, MA, 02643, United States
1.0k from Academy Playhouse center

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

1 Bedroom9 Guests
New to Booking
$363
Average price / night
Check Availability

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 Oceanfront Rentals in Academy Playhouse.

Academy Playhouse Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 692 verified oceanfront rentals in Academy Playhouse. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Academy Playhouse vary depending on the property size, exact beachfront location, and season. Rates typically start from around $257 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Academy Playhouse offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Academy Playhouse welcome pets. Currently, 31 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Academy Playhouse often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Ocean View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.