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

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  3.  USA

  4.  Massachusetts

  5.  Vineyard Haven
  6.  Vineyard Playhouse

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707 Best Vacation Rentals in Vineyard Playhouse (Starting from $174)

Island Time
Island Time
House
Vineyard Haven, MA, USA
0.3k from Vineyard Playhouse center

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

1 Bedroom4 Guests
8.8

Fabulous

13 reviews

$197
Average price / night
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Make 'Our Place' Your Place for Summer Vacation!
Make 'Our Place' Your Place for Summer Vacation!
House
Vineyard Haven, MA, 02568, United States
0.1k from Vineyard Playhouse center

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

3 Bedrooms7 Guests
9.8

Exceptional

9 reviews

$462
Average price / night
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Main Street Upper
Main Street Upper
Apartment
Vineyard Haven, MA, USA
0.4k from Vineyard Playhouse center

Apartments, Accommodations, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms7 Guests
7.6

Good

15 reviews

$510
Average price / night
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Pristine  with central air and outdoor shower
Pristine with central air and outdoor shower
House
Vineyard Haven, MA, 02568, United States
0.1k from Vineyard Playhouse center

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

3 Bedrooms8 Guests
9.6

Exceptional

27 reviews

$578
Average price / night
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Family Getaway Walkable to Town
Family Getaway Walkable to Town
House
Vineyard Haven, MA, USA
0.5k from Vineyard Playhouse center

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

3 Bedrooms8 Guests
1.0

Review score

1 reviews

$1219
Average price / night
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Stylish In-Town Cottage- Walk to everything!
Stylish In-Town Cottage- Walk to everything!
House
Vineyard Haven, MA, 02568, United States
0.1k from Vineyard Playhouse center

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

1 Bedroom2 Guests
10.0

Exceptional

12 reviews

$894
Average price / night
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Vineyard Harbor Motel
Vineyard Harbor Motel
Apartment
Ferry Boat Island, MA, USA
0.5k from Vineyard Playhouse center

Apartments, Cheap, Accommodations, Parking, Serviced apartments, Lodgings, Beach, Places to stay

1 Bedroom2 Guests
9.7

Exceptional

3 reviews

$341
Average price / night
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Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly
Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly
House
Tisbury, MA, 02568, United States
0.1k from Vineyard Playhouse center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Fireplace, Free Parking, Heater

9 Bedrooms18 Guests
10.0

Exceptional

68 reviews

$1429
Average price / night
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Everyday is Saturday
Everyday is Saturday
Apartment
Vineyard Haven, MA, USA
0.7k from Vineyard Playhouse center

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

3 Bedrooms6 Guests
7.4

Good

6 reviews

$439
Average price / night
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6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
House
Tisbury, MA, 02568, United States
0.2k from Vineyard Playhouse center

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

6 Bedrooms13 Guests
10.0

Exceptional

3 reviews

$1710
Average price / night
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Modern Family Home Walkable to Town
Modern Family Home Walkable to Town
House
Vineyard Haven, MA, USA
0.8k from Vineyard Playhouse center

View, Internet, Fireplace/Heating, Air Conditioner, Security/Safety, Child Friendly

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$760
Average price / night
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Greek Revival-Inspired In-Town Luxury Getaway
Greek Revival-Inspired In-Town Luxury Getaway
House
Vineyard Haven, MA, 02568, United States
0.2k from Vineyard Playhouse center

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

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$917
Average price / night
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Island Home
Island Home
House
Vineyard Haven, MA, USA
0.8k from Vineyard Playhouse center

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

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$652
Average price / night
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Captain Spring House: In Town Luxury - Water Views - Walk to Ferry!
Captain Spring House: In Town Luxury - Water Views - Walk to Ferry!
House
Vineyard Haven, MA, 02568, United States
0.2k from Vineyard Playhouse center

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

4 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$909
Average price / night
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The Ferry Sanctuary
The Ferry Sanctuary
House
Vineyard Haven, MA, USA
1.0k from Vineyard Playhouse center

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

4 Bedrooms8 Guests
2.0

Review score

1 reviews

$960
Average price / night
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Downtown brand new construction 3 bed & 3 bath
Downtown brand new construction 3 bed & 3 bath
House
Tisbury, MA, 02568, United States
0.3k from Vineyard Playhouse center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1835
Average price / night
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Family-Friendly Tisbury Escape - Walk to Town
Family-Friendly Tisbury Escape - Walk to Town
House
Vineyard Haven, MA, USA
1.3k from Vineyard Playhouse center

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

5 Bedrooms8 Guests
9.5

Superb

4 reviews

$273
Average price / night
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Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
Stunning, Classic Renovated Greek Revival - few mins Walk to Main St & VH Ferry
House
Vineyard Haven, MA, 02568, United States
0.3k from Vineyard Playhouse center

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

4 Bedrooms10 Guests
10.0

Exceptional

42 reviews

$1143
Average price / night
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Easy Access to Beaches Vineyard Haven House
Easy Access to Beaches Vineyard Haven House
House
Vineyard Haven, MA, USA
1.5k from Vineyard Playhouse center

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

3 Bedrooms6 Guests
New to Booking
$491
Average price / night
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12 mins from Beach - Immaculate Intimate Retreat!
12 mins from Beach - Immaculate Intimate Retreat!
Apartment
Tisbury, MA, 02568, United States
0.3k from Vineyard Playhouse center

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

2 Bedrooms4 Guests
10.0

Exceptional

35 reviews

$356
Average price / night
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Cozy Vineyard Haven Cottage Less Than 1 Mi to Beach!
Cozy Vineyard Haven Cottage Less Than 1 Mi to Beach!
House
Vineyard Haven, MA, USA
1.5k from Vineyard Playhouse center

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

1 Bedroom2 Guests
New to Booking
$174
Average price / night
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Beautiful, sunny historic home, walk from VH ferry!
Beautiful, sunny historic home, walk from VH ferry!
House
Tisbury, MA, 02568, United States
0.3k from Vineyard Playhouse center

Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms8 Guests
9.4

Superb

3 reviews

$958
Average price / night
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Updated Vineyard Farmhouse - Walk to Town & Ferry
Updated Vineyard Farmhouse - Walk to Town & Ferry
House
Tisbury, MA, 02568, United States
0.4k from Vineyard Playhouse center

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

4 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$698
Average price / night
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4-bedroom house in charming Vineyard Haven, easy walk to ferry, town and beaches
4-bedroom house in charming Vineyard Haven, easy walk to ferry, town and beaches
House
Vineyard Haven, MA, 02568, United States
0.4k from Vineyard Playhouse center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking

4 Bedrooms8 Guests
New to Booking
$844
Average price / night
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Classic Downtown Property
Classic Downtown Property
House
Tisbury, MA, 02568, United States
0.4k from Vineyard Playhouse center

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

3 Bedrooms8 Guests
10.0

Exceptional

64 reviews

$796
Average price / night
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Sea Captain's Victorian studio bedroom apartment.  Pets OK
Sea Captain's Victorian studio bedroom apartment. Pets OK
Apartment
Tisbury (Vineyard Haven), MA, 02568, United States
0.4k from Vineyard Playhouse center

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

1 Bedroom2 Guests
10.0

Exceptional

80 reviews

$230
Average price / night
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Historic Waterfront Home in Downtown VH — Bedroom AC window units
Historic Waterfront Home in Downtown VH — Bedroom AC window units
House
Vineyard Haven, MA, 02568, United States
0.4k from Vineyard Playhouse center

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

6 Bedrooms12 Guests
10.0

Exceptional

17 reviews

$925
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 in Vineyard Playhouse.

Where to stay in Vineyard Playhouse? Best neighborhoods & areas

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Frequently Asked Questions

You can explore 707 verified vacation rentals in Vineyard 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 Vineyard Playhouse vary depending on the season, property size, and location. Rates typically start from around $174 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 Vineyard 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 Vineyard Playhouse welcome pets. Currently, 19 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 Vineyard Playhouse often include amenities such as Fireplace/Heating, Laundry, and View. 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.