Winter Guide ~ Lodging

Provincetown Winter ~ Snowy beach in the center of Town

Provincetown’s beautiful Town Hall decorated for Holidays and New Year’s Celebrations!

Provincetown Winter ~ Waterfront with Provincetown Library

Come visit us this time of year when prices are very reasonable and spend an evening or more in one of our many lovely guesthouses & inns, one of our newly renovated hotels or pick a cozy apartment or condo for a longer stay…

Apartments, Condos, Houses… Sweet dreams!

Featured

Aerie House

Listing Title

Aerie House

184 Bradford Street, Provincetown, MA, 02657

www.aeriehouse.com

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Offering spectacular bay views from our hilltop Guesthouse centrally located in Provincetown’s charming East End Gallery and Restaurant District.

Last Minute Availability

6/13/2025 - $260-$410 Private Bath, Apartment, Junior Suite
6/14/2024 - $260-$410 Private Bath, Apartment, Junior Suite
6/15/2025 - $190-$260 Private Bath, Apartment, Junior Suite
6/16/2025 - $190-$350 Private Bath, Apartment, Junior Suite, 2 Bedroom Suite
6/17/2025 - $190-$350 Private Bath, Apartment, Junior Suite, 2 Bedroom Suite
6/18/2025 - $190-$350 Private Bath, Apartment, 2 Bedroom Suite
6/19/2025 - Sorry, Fully Booked
6/20/2025 - Sorry, Fully Booked
6/21/2025 - $385 Junior Suite
6/22/2025 - $190-$350 Private Bath, Junior Suite, 2 Bedroom Suite
6/23/2025 - $190-$350 Private Bath, 2 Bedroom Suite
6/24/2025 - $190-$350 Private Bath, 2 Bedroom Suite
6/25/2025 - $190 Private Bath
6/26/2025 - $190 Private Bath

Featured

Angel’s Landing

Listing Title

Angel’s Landing

353 Commercial Street, Provincetown, MA 02657

www.angelslandingptown.net

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Angels' Landing is a group of individual condominiums located on the bay, in the center of Provincetown.

Last Minute Availability

Short term (nightly and weekly) and long term (monthly) rentals available.
6/2/25 - $200-$400- Condo with private bath.
6/3/25 - $200-$400- Condo with private bath.
6/4/25 - $200-$400- Condo with private bath.
6/5/25 - $200-$400- Condo with private bath.
6/6/25 - $200-$400- Condo with private bath.
6/7/25 - $200-$400- Condo with private bath.
6/8/25 - $200-$400- Condo with private bath.
6/9/25 - $200-$400- Condo with private bath.
6/10/25 - $200-$400- Condo with private bath.
6/11/25 - $200-$400- Condo with private bath.
6/12/25 - $200-$400- Condo with private bath.
6/13/25 - $200-$400- Condo with private bath.
6/14/25 - $200-$400- Condo with private bath.

Featured

Land’s End Inn

Listing Title

Land’s End Inn

22 Commercial Street, Provincetown, MA, 02657

www.landsendinn.com

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Set high atop Gull Hill in Provincetown’s charming West End, Land’s End Inn offers luxurious accommodations with panoramic ocean views.

Last Minute Availability

5/26- $275-545
5/27- $275-545
5/28- $275-545
5/29- $275-545
5/30- $450-625
5/31- $475-625
6/1 - $295-545
6/2 - $295-545
6/3 - $395-545
6/4 - $395-545
6/5 - $295-395
6/6 - $425-450
6/7 - $425-525
6/8 - $375-670

Featured

Masthead Resort & Cottages

Listing Title

Masthead Resort & Cottages

31-41 Commercial Street, Provincetown, MA, 02657

www.themasthead.com

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Distinctive accommodations on Provincetown Harbor. Every cottage faces the water.

Featured

Somerset House Inn

Listing Title

Somerset House Inn

378 Commercial Street, Provincetown, MA, 02657

www.somersethouseinn.com

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Approachable luxury accommodations, centrally located on Commercial Street in Provincetown.

Featured

Watermark Inn

Listing Title

Watermark Inn

603 Commercial Street, Provincetown, MA, 02657

www.watermark-inn.com

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Located directly on Cape Cod Bay in the quiet East End. We have been family-owned and operated since 1983.

Featured

Watership Inn

Listing Title

Watership Inn

7 Winthrop Steet, Provincetown, MA, 02657

www.watershipinn.com

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Ideally located on a quiet side street yet within a few minute walk to all there is to see and do in Provincetown.

Last Minute Availability

6/1 $125-$259 Full, Queen, Suite, Apartment with private bath
6/2 $125- $259 Full, Queen, Suite, Apartment with private bath
6/3 $125- $259 Full, Queen, Suite, Apartment with private bath
6/4 $125- $259 Full, Queen, Suite, Apartment with private bath
6/5 $125- $259 Full, Queen, Suite, Apartment with private bath
6/6 $125- $259 Full, Queen, Apartment with private bath
6/7 $125- $259 Full, Apartment with private bath
6/8 $125- $259 Full, Queen, Apartment with private bath
6/9 $125- $259 Full, Queen, Apartment with private bath
6/10 $125- $259 Full, Queen, Apartment with private bath
6/11 $125- $259 Full, Queen, Apartment with private bath
6/12 $130- $288 Full, Queen, Apartment with private bath
6/13 $175- $288 Queen, Apartment with private bath
6/14 $130- $288 Full, Queen, Apartment with private bath

Featured

White Porch Inn

Listing Title

White Porch Inn

7 Johnson Street, Provincetown, MA, 02657

www.whiteporchinn.com

Provincetown’s unique, luxurious and newly renovated boutique hotel just steps away from Commercial Street & the center of town.

Last Minute Availability

Queen or king rooms with private bathrooms available ranging from $259 to $559 through the month of June. Please call or visit our website to book!

8 Dyer Hotel

Listing Title

8 Dyer Hotel

8 Dyer Street, Provincetown, MA, 02657

www.8dyer.com

At 8 Dyer Hotel, our modern 7-room guest house is tucked away on a quiet side street of one of the world’s most scenic and lively destinations – Provincetown.

Admiral’s Landing

Listing Title

Admiral’s Landing

158 Bradford Street, Provincetown, MA, 02657

www.admiralslanding.com

A Greek Revival home from the 1860’s, Admiral’s Landing offers a comfortable and relaxed atmosphere, in a convenient central location.

Benchmark Inn

Listing Title

Benchmark Inn

6 Dyer Street, Provincetown, MA, 02657

www.benchmarkinn.com

Award winning boutique style guest house. Seven superb accommodations, central A/C, gas fireplaces, spa tub and/or rain shower, dual entrance.

Brasswood Inn

Listing Title

Brasswood Inn

174 Commercial Street, Provincetown, MA, 02657

www.brasswoodptown.com

The Brasswood Inn is prominently located on Commercial Street in the West End of Provincetown and offers a warm, relaxed atmosphere where all are welcome.