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A harbor at dusk with boats docked, buildings, and a cloudy sky.
Photo by ‎Bill England
Open Photo by ‎Bill England

Princetown Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

Top Luxury vacation packages in Princetown

Price found within the past 48 hours. Click for updated prices.
  • Family Cottage | Living area | TV
    Sep 11 - Sep 14

    Pine Cottages + Flight

    Stanhope
    3 nights
    2.0 star property
    8.0/10 - Very Good (21 reviews)
    "We had a great stay at Pine Cottages. The cottage was extremely clean and it had everything we needed. You can tell that the owners are doing upgrades - the windows are new, for example. There was a delivery of shingles being made when we left. It is still an old- fashioned (“traditional”) cottage - lots of wood everywhere! The mattresses could be better but I had good sleeps on them. The bathroom was very tiny. Very close to the beach if that is something you are interested in. We would stay..."
    Reviewed July 24, 2026
    Roundtrip • Boston (BOS) - Charlottetown (YYG)
    BOS - YYG • 2 stops YYG - BOS • 1 stop
    $998
    $910
    per traveler
    found 19 hours ago
    Pine Cottages
  • Lobby
    Sep 11 - Sep 14

    The Hotel on Pownal + Flight

    Downtown Charlottetown
    3 nights
    2.5 star property
    8.8/10 - Excellent (1,007 reviews)
    "Although the property is well located, the quality and cleanliness of the room, particularly in relation to the price we paid was poor."
    Reviewed July 26, 2026
    Roundtrip • Boston (BOS) - Charlottetown (YYG)
    BOS - YYG • 2 stops YYG - BOS • 1 stop
    $1,170
    $1,018
    per traveler
    found 19 hours ago
    The Hotel on Pownal
  • Front of property
    Sep 11 - Sep 14

    The Great George + Flight

    Downtown Charlottetown
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,009 reviews)
    "Unique Breakfast"
    Reviewed July 25, 2026
    Roundtrip • Boston (BOS) - Charlottetown (YYG)
    BOS - YYG • 2 stops YYG - BOS • 1 stop
    $1,608
    $1,446
    per traveler
    found 19 hours ago
    The Great George
  • Rooftop terrace
    Sep 11 - Sep 14

    Rodd Charlottetown + Flight

    Downtown Charlottetown
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,013 reviews)
    "Best hotel for couples"
    Reviewed July 25, 2026
    Roundtrip • Boston (BOS) - Charlottetown (YYG)
    BOS - YYG • 2 stops YYG - BOS • 1 stop
    $1,321
    $1,198
    per traveler
    found 19 hours ago
    Rodd Charlottetown
  • The Lookout Suite | Down comforters, WiFi (free)
    Oct 18 - Oct 24

    The Cliffside Inn + Flight

    Little Sands
    6 nights
    3.0 star property
    8.8/10 - Excellent (70 reviews)
    Roundtrip • Providence (PVD) - Charlottetown (YYG)
    PVD - YYG • 2 stops YYG - PVD • 2 stops
    $1,588
    $1,455
    per traveler
    found 1 day ago
    The Cliffside Inn

Top Luxury Princetown Hotels

Exterior

Suite 1 - Older/Simple/Rustic/No Frills/Budget 2BR - Near Cabot Beach Park

Suite 1 - Older/Simple/Rustic/No Frills/Budget 2BR - Near Cabot Beach Park
< 0.1 mi from Princetown
10.0 out of 10, Exceptional, (1 review)
"Great place to stay!"
$125 nightly
The price is $144
Jul 30 - Jul 31
Total with taxes and fees
Suite 1 - Older/Simple/Rustic/No Frills/Budget 2BR - Near Cabot Beach Park
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.
See all properties in Princetown

All you need to know about luxury vacations in Princetown

What can I expect from a luxury Princetown vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Princetown vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Princetown?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Princetown luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $910. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Princetown?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Princetown with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Princetown?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Princetown with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Princetown with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.