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

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1173 Best Vacation Rentals in Academy Playhouse (Starting from $190)

Walk to Town Fully Renovated
Walk to Town Fully Renovated
Apartment
Orleans, MA, USA
0.3k from Academy Playhouse center

Apartments, Accommodations, Parking, Lodgings, Places to stay

6 Bedrooms12 Guests
New to Booking
$1656
Average price / night
Check Availability
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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Paradise On Cape Cod
Paradise On Cape Cod
House
Orleans, MA, USA
0.5k from Academy Playhouse center

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

4 Bedrooms8 Guests
7.5

Good

4 reviews

$1451
Average price / night
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Central AC Close to Nauset Beach
Central AC Close to Nauset Beach
House
Orleans, MA, USA
0.8k from Academy Playhouse center

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

4 Bedrooms10 Guests
New to Booking
$681
Average price / night
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Charming 6BR Orleans Retreat, Great Outdoor Space, Walk to Orleans Town
Charming 6BR Orleans Retreat, Great Outdoor Space, Walk to Orleans Town
House
Orleans, MA, 02653, United States
0.4k from Academy Playhouse center

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

6 Bedrooms14 Guests
New to Booking
$903
Average price / night
Check Availability
Waterfront on Orleans Cove
Waterfront on Orleans Cove
House
Orleans, MA, USA
0.8k from Academy Playhouse center

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

3 Bedrooms7 Guests
New to Booking
$488
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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Babes Bungalow by Leavetown Vacations
Babes Bungalow by Leavetown Vacations
House
Orleans, MA, USA
0.9k from Academy Playhouse center

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

1 Bedroom2 Guests
8.5

Very Good

2 reviews

$455
Average price / night
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Quaint Cape Near Beaches And Centrally Located
Quaint Cape Near Beaches And Centrally Located
House
Orleans, MA, 02653, United States
0.6k from Academy Playhouse center

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

3 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$294
Average price / night
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10 ft from Crystal Lake New renovation
10 ft from Crystal Lake New renovation
House
Orleans, MA, USA
0.9k from Academy Playhouse center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1303
Average price / night
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Mid-Century Contemporary
Mid-Century Contemporary
House
Orleans, MA, 02653, United States
0.6k from Academy Playhouse center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
New to Booking
$588
Average price / night
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Mins to Nauset Beach & Walkable to Town
Mins to Nauset Beach & Walkable to Town
House
Orleans, MA, USA
1.0k from Academy Playhouse center

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

3 Bedrooms8 Guests
New to Booking
$583
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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Town Cove Oyster House
Town Cove Oyster House
House
Eastham, MA, USA
1.3k from Academy Playhouse center

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

3 Bedrooms6 Guests
7.0

Good

1 reviews

$698
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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Fantastic Home by Eldridge Park
Fantastic Home by Eldridge Park
House
Orleans, MA, USA
1.3k from Academy Playhouse center

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

3 Bedrooms6 Guests
New to Booking
$190
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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Amazing Outdoor Space Access to Town Cove
Amazing Outdoor Space Access to Town Cove
House
Orleans, MA, USA
1.3k from Academy Playhouse center

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

5 Bedrooms12 Guests
9.0

Fabulous

1 reviews

$1424
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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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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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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Ocean Views New A C Dog Welcome
Ocean Views New A C Dog Welcome
House
Eastham, MA, USA
1.5k from Academy Playhouse center

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

5 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$1888
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
Check Availability
Cute Cottage Living by the Sea
Cute Cottage Living by the Sea
House
Eastham, MA, USA
1.5k from Academy Playhouse center

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

1 Bedroom2 Guests
7.7

Good

3 reviews

$344
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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Newly updated spacious steps to water
Newly updated spacious steps to water
House
Eastham, MA, USA
1.5k from Academy Playhouse center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$513
Average price / night
Check Availability
Central location! Bungalow for 2 + Garden
Central location! Bungalow for 2 + Garden
House
Orleans, MA, 02653, United States
0.9k from Academy Playhouse center

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

1 Bedroom2 Guests
9.6

Exceptional

5 reviews

$317
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 Vacation Rentals in Academy Playhouse.

Academy Playhouse Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1173 verified vacation rentals in Academy Playhouse. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Academy Playhouse vary depending on the season, property size, and location. Rates typically start from around $190 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Academy Playhouse include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Academy Playhouse welcome pets. Currently, 51 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Academy Playhouse often include amenities such as Fireplace/Heating, View, and Internet. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.