Festive Fire & Ice: Holiday Hotels with Flexible Cancellation Policies

Courtesy Chatham Bars Inn

Somehow - impossibly - it’s time to stow the beach chairs back in the garage and trade swimsuits for school books. You know any day now you’re going to walk into Starbucks for your morning coffee and BAM! the Pumpkin Spice onslaught will have begun, and your whole Instagram feed will fill with people going apple picking while wearing flannel; then it’s just a matter of time before Mariah Carey’s insisting that all she wants for Christmas is you (on loop). So while we’re still pumping the A/C and savoring the last few evenings of rosé on the porch, it’s time to start thinking about where you want to wake up in that stretch of time between Christmas and the new year.

If you’re anything like the TLF team, you’re itching to travel, but then again 2020 has given us all trust issues and it’s hard to make a commitment. So whether you’re going to power through the last quarter of the year dreaming of sand beneath your toes or powder beneath your skis, we’ve rounded up our favorite properties that understand it’s tough to commit right now and have adjusted their cancellation policies accordingly. Feel free to plan with confidence - we all deserve something to look forward to.


Heat Things Up

Leave the dashing through the snow to someone else - these hot spots are for the “have bikini, will travel” crowd.

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Four Seasons Surf Club

Surfside, Florida | Art Deco glamour and au-courant Miami style, beachfront.
Rates from:
available upon request
Deposit: 25% deposit required at time of booking, refundable until 30 days prior
Cancellation: Full balance due 30 days prior to arrival, at which time the stay becomes fully non-refundable


ROSEWOOD MIRAMAR BEACH

Santa Barbara, California | East coast beach chic meets California cool, with Santa Barbara's best beachfront rooms.
Rates from:
$955 per room per night
Deposit: Credit card required to hold room at time of booking
Cancellation: Cancel 24 hours prior to avoid full penalty of stay


BEVERLY HILLS HOTEL

Beverly Hills, California | Live your Hollywood (and Instagram) dreams at this California classic.
Rates from: $645 per room per night
Deposit: Credit card required to hold room at time of booking
Cancellation: Cancel 24 hours prior to avoid full penalty of stay


AMANYARA

Turks & Caicos | Impeccable imported materials make you feel you've traveled beyond the Caribbean.
Rates from: $3,100 per suite per night
Deposit: 50% deposit at time of booking
Cancellation: Full amount taken 30 days prior to arrival, at which point the booking becomes non-refundable


AMANera

Dominican Republic | Clifftop casitas offer uninterrupted views of Playa Grande Beach.
Rates from: $2,329 per suite per night
Deposit: 3 night deposit at time of booking, refundable until October 1
Cancellation: Full booking nonrefundable from October 1


LE TOINY

St. Barth's | A discreet hideaway on the wilder side of St Barth's
Rates from: $3,354 per room per night
Deposit: 3 night deposit at time of booking; Balance taken September 15
Cancellation: 3% fee up to 61 days prior to arrival; Deposit retained if canceled 60-31 days prior. 100% penalty within 30 days


Como Parrot Cay

Turks & Caicos | A once uninhabited island turned minimalist wellness retreat
Rates from: $2,400 per room per night
Deposit: One night deposit at time of booking; refundable until September 1st
Cancellation: Full booking nonrefundable from September 1


LE BARTHELEMY

St. Barth's | Contemporary and spacious option with jaw-dropping ocean views
Rates from: $2,555 per room per night
Deposit: 30% deposit required to book
Cancellation: Remaining balance taken on October 15, at which point the booking becomes nonrefundable


HOTEL ESENCIA

Quintana Roo, Mexico | Formerly the home of an Italian duchess,now a boho palapa paradise
Rates from: $2,100 per room per night
Deposit: 50% deposit to book; balance will be charged 95 days prior to arrival
Cancellation: Until September 20, 10% cancellation fee; After September 20, fully non-refundable


ROSEWOOD MAYAKOBA

Playa del Carmen, Mexico | Lagoons, canals, & endless ocean lend a sense of adventure to this ideal family destination
Rates from: $1,965 per room per night
Deposit: 2-night non-refundable deposit
Cancellation: Full amount taken 90 days prior to arrival, at which point the booking becomes non-refundable


LAS VENTANAS AL PARAISO

San José del Cabo, Mexico | "Windows to paradise" overlooking the vibrant Sea of Cortez.
Rates from: $1,976 per room per night
Deposit: Deposit equal to full stay due upon booking
Cancellation: Deposit refundable until 90 days prior to arrival


FOUR SEASONS CABO

Baja California Sur, Mexico | Somehow, Four Seasons has managed to find a part of Cabo that feels undiscovered
Rates from: $1,850 per room per night
Deposit: 2-night nonrefundable deposit
Cancellation: Full amount taken 90 days prior to arrival, at which point the booking becomes non-refundable


Keep It Cool

Because you’re dreaming of a white Christmas… and Boxing Day… and New Year’s Eve… and New Year’s Day…

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THE LODGE AT BLUE SKY

Just outside Park City, Utah | Ski Park City, shoot clay pigeons, & sip local whiskey
Rates from: $1,499 per room per night
Deposit: 50% deposit due upon booking, refundable until 30 days prior
Cancellation: Full non-refundable balance due 30 days prior


AMANGIRI

Canyon Point, Utah | Simply one of the best hotels anywhere, no matter the season
Rates from: $2,000 per room per night (all inclusive)
Deposit: 50% deposit due upon booking, refundable until 45 days prior
Cancellation: Full non-refundable balance due 45 days prior


AMANGANI

Jackson, Wyoming | Soothing decor on an epic scale in one of the world's most beautiful places
Rates from: $1,420 per room per night
Deposit: 50% deposit due upon booking, refundable until November 1
Cancellation: Full balance due November 1, at which time the stay becomes fully non-refundable


CALDERA HOUSE

Teton Village, Wyoming | Soak up the action in the center of Teton Village in suites perfect for families
Rates from: Two bedroom suites from $8,000 per night
Deposit: 20% non-refundable deposit
Cancellation: Full amount taken 45 days prior to arrival, at which point the booking becomes non-refundable


MONTAGE DEER VALLEY

Deer Valley, Utah | Ski in/ski out access tucked among snowy pine trees
Rates from: $1,265 per room per night
Deposit: Two night deposit due at time of booking. Full payment due 45 days prior.
Cancellation: Full balance due 45 days prior to arrival, at which time the stay becomes fully non-refundable


THE LITTLE NELL

Aspen, Colorado | The best address in Aspen, for skiing and for socializing.
Rates from: $2,228 per room per night
Deposit: 2-night non-refundable deposit due upon booking
Cancellation: Full non-refundable balance due September 1


ST REGIS ASPEN

Aspen, Colorado | Colorado coziness a short walk from the gondolas and other Aspen action
Rates from: $2,700 per room per night
Deposit: Credit card to hold
Cancellation: Full amount taken 45 days prior to arrival, at which point the booking becomes non-refundable


FOUR SEASONS VAIL

Vail, Colorado | Four Seasons treatment in the middle of the Colorado rockies.
Rates from: $1,561 per room per night
Deposit: 50% non-refundable deposit due at time of booking
Cancellation: Full non-refundable balance due September 1


TWIN FARMS

Barnard, Vermont | Ski 6 private runs, accessible only by chauffeured snowmobile
Rates from: $2,900 per room per night (all inclusive)
Deposit: $500 per night deposit per room
Cancellation: Amount due in full at 60 days; at that point becomes nonrefundable


BLACKBERRY FARM

Walland, Tennessee | Bucolic woodland surroundings and legendary cuisine
Rates from: $1,445 per room per night (all inclusive)
Deposit: 2 night deposit; refundable until 30 days prior
Cancellation: Full non-refundable amount taken 30 days prior to arrival


Blackberry Mountain

Walland, Tennessee | The wilder younger sister, who's into ceramics and foraging
Rates from: $1,795 per room per night (all inclusive)
Deposit: 2 night deposit; refundable until 30 days prior
Cancellation: Full non-refundable amount taken 30 days prior to arrival