Academy Playhouse

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Orleans Travel Guide

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Price found within the past 48 hours. Click for updated prices.

The Colonnade Hotel Back Bay

Back Bay

￥271,020

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Tokyo (HND) to Boston (BOS)

9.2/10 Wonderful! (2,268 reviews)

Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 2026

Raffles Boston

Back Bay

￥420,211

per person

Mar 26 - Mar 30

found 17 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Boston (BOS)

9.6/10 Exceptional! (181 reviews)

Attention to guest needs.

Reviewed on Feb 8, 2026

The Whitney Hotel

Beacon Hill

￥329,892

per person

Mar 26 - Mar 30

found 16 hours ago

Roundtrip non-stop flight included

Tokyo (HND) to Boston (BOS)

9.6/10 Exceptional! (482 reviews)

Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 2026

Popular places to visit

This windmill was built in the early 1700's in South Orleans. By 1839 it was moved to overlook the Town Cove on the present hillside site of The Governor Prence Motor Inn on Rt 6A. During the recent restoration it was relocated to the small park on the shore of Town Cove where it stands today.

Jonathan Young Windmill

Jonathan Young Windmill is just one of the places to see in Orleans, so why not enjoy the other things to explore during your travels? Stroll along the seaside or seek out the hiking trails.

An evening at the Cape is just what the weather gods recommend. Come summer and most Bostonians don't lose a single opportunity to hit the coastline. These miles of pristine beaches make 100 days of summer absolutely worthwhile. Most people have a few cape stories, and so do we. Hoping to share them with you all over this summer.

#CapeCod #VisitMA

Rock Harbor Beach

Why not spend a lazy afternoon at Rock Harbor Beach during your trip to Orleans?

Skaket Beach

4.5/5(18 reviews)

Warm, clear waters make this beach destination ideal for casual swimming, watersports or a restorative rest on the white sandy shore.

stony rock pier, ocean boardwalk, off-centered

Stony Island

Commune with nature and explore the great outdoors at Stony Island during your travels in Eastham. Amble around the area's beautiful beaches or seek out the biking trails.

First Encounter Beach

Why not spend a lazy afternoon at First Encounter Beach during your trip to Eastham? Amble around the area's beautiful beaches or seek out the biking trails.

Orleans Historical Society Meeting House Museum

You can spend an afternoon studying the exhibits at Orleans Historical Society Meeting House Museum in Orleans. Wander the beautiful beaches and seaside in this family-friendly area.

Best Lodging Options Near Academy Playhouse

Check availability on hotels close to Academy Playhouse

Walk to Town, Fully Renovated!

Orleans MA

Historic charmer on the water with a firepit, kayaks, bikes, & firepit

Eastham MA

Tranquil & sunlit home with peaceful yard, large deck, & fireplace - near beach

Orleans MA

Waterfront Fun at this Huge Family Estate!

Eastham MA

Child Friendly, Charming 3-Bedroom Cape in Unbeatable Location

Orleans MA

Tonset Manor: 232-O East Orleans Vacation Estate Includes Guest House, Heated Pool, Hot Tub

Orleans MA

Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

Eastham MA

Sleeps 8, Minutes to Nauset Beach!

Orleans MA

New Saltwater Heated Pool & Hot Tub -Less than 5 Minutes from Nauset Beach!

Orleans MA

See all 3,244 properties in Academy Playhouse

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.