First Encounter Beach Tours and Activities

Photo by Tony Ning
Photo by Tony Ning

Plan a trip to see First Encounter Beach

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

Raffles Boston

5 out of 5
Back Bay
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.4/10 Exceptional! (435 reviews)
Not my favorite Four Seasons. I requested that they remove any alcohol from my room and they didn’t accommodate that simple request. They seemed hurried. B-

Reviewed on Jun. 22, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on Jul. 25, 2025

Popular places to visit

Skaket Beach which includes a sandy beach as well as a family

Skaket Beach

4/5(1 review)

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

Skaket Beach
Jonathan Young Windmill

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 beautiful beaches or seek out the hiking trails.

Jonathan Young Windmill
Edward Penniman House and Barn

Edward Penniman House and Barn

You can spend an afternoon studying the exhibits at Edward Penniman House and Barn in Eastham. Stroll along the seaside or seek out the hiking trails.

Edward Penniman House and Barn
Salt Pond Visitor Center

Salt Pond Visitor Center

If you want to learn more about Cape Cod National Seashore or simply need facilities, make this state-of-the-art visitor center in Eastham your first stop.

Salt Pond Visitor Center

Herring Brook Beach

Why not spend a lazy afternoon at Herring Brook Beach during your trip to North Eastham? Wander the beautiful beaches in this family-friendly area.

Herring Brook Beach

Rock Harbor Beach

Why not spend a lazy afternoon at Rock Harbor Beach during your trip to Orleans? Stroll along the area's beaches or simply enjoy its seafood restaurants.

Rock Harbor Beach

Best Lodging Options Near First Encounter Beach

Bayfront cottage w/ bluffside deck & outdoor shower - steps to private beach

Bayfront cottage w/ bluffside deck & outdoor shower - steps to private beach

Eastham
Bayfront cottage w/ bluffside deck & outdoor shower - steps to private beach
Whalewalk Inn and Spa

Whalewalk Inn and Spa

3.5 out of 5
220 Bridge Road, Eastham, MA
Whalewalk Inn and Spa
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
Captains Quarters Motel & Conference Center
Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod

2 out of 5
48 Cranberry Hwy, Orleans, MA
Rodeway Inn Orleans - Cape Cod
Light-filled home steps from Rail Trail - near pond, bay & ocean beaches

Light-filled home steps from Rail Trail - near pond, bay & ocean beaches

Eastham
Light-filled home steps from Rail Trail - near pond, bay & ocean beaches
Endless Dunes, A Modern Motel

Endless Dunes, A Modern Motel

2 out of 5
3620 State Highway, Eastham, MA
Endless Dunes, A Modern Motel
Eagle Wing Inn - Cape Cod

Eagle Wing Inn - Cape Cod

3 out of 5
960 State Highway, Route 6, Eastham, MA
Eagle Wing Inn - Cape Cod
Cozy Cape Cottage with Beach Access

Cozy Cape Cottage with Beach Access

Eastham
Cozy Cape Cottage with Beach Access
Viking Shores Motor Inn

Viking Shores Motor Inn

2 out of 5
5200 State Highway Rte 6, Eastham, MA
Viking Shores Motor Inn
See all 3,054 properties in First Encounter Beach
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.