Rooms & Cottages

At the Pridwin

The Pridwin’s accommodations provide true Shelter Island luxury. Inside our historic hotel, each guest room features nautical accents throughout—a nod to the Pridwin’s location perched on a rise overlooking Crescent Beach. For guests looking for a little more elbow room, The Pridwin Cottages offer a spacious and private stay, complete with private decks, living areas and gas fireplaces.

Select Your Accommodations:


Guest Rooms Cottages View All
floor plan of Pridwin guest accommodations

Hillside Room

One King Bed

215 ft²

Equal parts cozy and classic, our sunny south-facing Hillside Rooms feature one King bed and views of the greenery and cottages nestled around the Pridwin grounds.

Book Now
floor plan of Pridwin guest accommodations

Waterview Room

One King Bed

215 ft²

Our Waterview Rooms feature one plush King-size bed and breathtaking views of Crescent Beach. Take in a sunset over Long Island Sound—all from the comfort of your guestroom.

Book Now
floor plan of Pridwin guest accommodations

Corner Preferred Room

One King Bed | Queen Sleeper Sofa

230 ft²

Spacious and filled with natural light, our Corner Preferred Rooms feature windows on two sides of the guest room, enabling gorgeous water views of Crescent Beach and Long Island sound. Each Corner Preferred Room is furnished with one King-size bed, as well as a Queen sleeper sofa.

Book Now
floor plan of Pridwin guest accommodations

Terrace Room

One King Bed | Queen Sleeper Sofa

230 ft²

Located on the ground floor of the hotel, our spacious Terrace rooms feature an outdoor deck with breathtaking views of Crescent Beach. Each Terrace Room is furnished with one King-size bed, as well as a Queen sleeper sofa.

Book Now
floor plan of Pridwin guest accommodations

Birch Cottage

Studio-Style Cottages | One Bedroom | Dog Friendly

529 ft² (interior and deck)

Quaint and well-appointed, our Birch Cottages offer private pet-friendly studio-style accommodations. Each Birch Cottage features a kitchenette, a Full-size sleeper sofa, a gas fireplace and a private deck overlooking Crescent Beach.

Book Now
floor plan of Pridwin guest accommodations

Hickory Cottage

Studio-Style Cottages | One Bedroom

620 ft² (interior and deck)

Our Hickory Cottages offer private studio-style accommodations with excellent water views overlooking Crescent Beach. Each Hickory Cottage features a kitchenette, a Full-size sleeper sofa, a gas fireplace and a private deck.

Book Now
floor plan of Pridwin guest accommodations

Larch Cottage

Studio-Style Cottages | One Bedroom

645 ft² (interior and deck)

Our Larch Cottages are perfect for families and groups looking for more space to relax. Each Larch Cottage features a bedroom with a King-size bed, a separate living room with a Full-size sleeper sofa, a kitchenette, a gas fireplace and a private deck with partial water views overlooking Crescent Beach.

Book Now
floor plan of Pridwin guest accommodations

Red Oak Cottage

Studio-Style Cottages | One Bedroom

860 ft² (interior and deck)

Our Red Oak cottages sport excellent water views overlooking Crescent Beach and Shelter Island Sound. Each Red Oak Cottage features a bedroom with a King-size bed, a separate living room with a Full-size sleeper sofa, a kitchenette, a gas fireplace and a private deck.

Book Now
floor plan of Pridwin guest accommodations

White Oak Cottage

Lofted Cottages | Two Bedrooms

1120 ft² (interior and deck)

Spacious and well-appointed, our White Oak cottages feature living rooms with double-height ceilings, a bedroom with King bed, a Full-size sleeper sofa, a lofted second-floor bedroom and bathroom, a kitchenette, a gas fireplace and a private deck overlooking Crescent Beach.

Book Now
floor plan of Pridwin guest accommodations

Caroline Cottage

Multi-Room House | One Bedroom

930 ft² (interior and deck)

Private and secluded, The Caroline Cottage offers private house-style accommodations and views overlooking a wooded grove of trees. The Caroline Cottage features bedroom with a King-size bed, a separate living room with a Full-size sleeper sofa, a gas fireplace and a kitchenette with an apartment-size refrigerator.

Book Now
floor plan of Pridwin guest accommodations

Frasier Cottage

Multi-Room House | Two Bedrooms

1289 ft² (interior and deck)

Nestled amongst a wooded grove of trees, the Frasier Cottage offers private house-style accommodations. This two-bedroom, two-bathroom cottage features a kitchenette with an apartment-size refrigerator, spacious living accommodations and a gas fireplace.

Book Now
floor plan of Pridwin guest accommodations

Hillside Room

One King Bed

215 ft²

Equal parts cozy and classic, our sunny south-facing Hillside Rooms feature one King bed and views of the greenery and cottages nestled around the Pridwin grounds.

Book Now
floor plan of Pridwin guest accommodations

Waterview Room

One King Bed

215 ft²

Our Waterview Rooms feature one plush King-size bed and breathtaking views of Crescent Beach. Take in a sunset over Long Island Sound—all from the comfort of your guestroom.

Book Now
floor plan of Pridwin guest accommodations

Corner Preferred Room

One King Bed | Queen Sleeper Sofa

230 ft²

Spacious and filled with natural light, our Corner Preferred Rooms feature windows on two sides of the guest room, enabling gorgeous water views of Crescent Beach and Long Island sound. Each Corner Preferred Room is furnished with one King-size bed, as well as a Queen sleeper sofa.

Book Now
floor plan of Pridwin guest accommodations

Terrace Room

One King Bed | Queen Sleeper Sofa

230 ft²

Located on the ground floor of the hotel, our spacious Terrace rooms feature an outdoor deck with breathtaking views of Crescent Beach. Each Terrace Room is furnished with one King-size bed, as well as a Queen sleeper sofa.

Book Now
floor plan of Pridwin guest accommodations

Birch Cottage

Studio-Style Cottages | One Bedroom | Dog Friendly

529 ft² (interior and deck)

Quaint and well-appointed, our Birch Cottages offer private pet-friendly studio-style accommodations. Each Birch Cottage features a kitchenette, a Full-size sleeper sofa, a gas fireplace and a private deck overlooking Crescent Beach.

Book Now
floor plan of Pridwin guest accommodations

Hickory Cottage

Studio-Style Cottages | One Bedroom

620 ft² (interior and deck)

Our Hickory Cottages offer private studio-style accommodations with excellent water views overlooking Crescent Beach. Each Hickory Cottage features a kitchenette, a Full-size sleeper sofa, a gas fireplace and a private deck.

Book Now
floor plan of Pridwin guest accommodations

Larch Cottage

Studio-Style Cottages | One Bedroom

645 ft² (interior and deck)

Our Larch Cottages are perfect for families and groups looking for more space to relax. Each Larch Cottage features a bedroom with a King-size bed, a separate living room with a Full-size sleeper sofa, a kitchenette, a gas fireplace and a private deck with partial water views overlooking Crescent Beach.

Book Now
floor plan of Pridwin guest accommodations

Red Oak Cottage

Studio-Style Cottages | One Bedroom

860 ft² (interior and deck)

Our Red Oak cottages sport excellent water views overlooking Crescent Beach and Shelter Island Sound. Each Red Oak Cottage features a bedroom with a King-size bed, a separate living room with a Full-size sleeper sofa, a kitchenette, a gas fireplace and a private deck.

Book Now
floor plan of Pridwin guest accommodations

White Oak Cottage

Lofted Cottages | Two Bedrooms

1120 ft² (interior and deck)

Spacious and well-appointed, our White Oak cottages feature living rooms with double-height ceilings, a bedroom with King bed, a Full-size sleeper sofa, a lofted second-floor bedroom and bathroom, a kitchenette, a gas fireplace and a private deck overlooking Crescent Beach.

Book Now
floor plan of Pridwin guest accommodations

Frasier Cottage

Multi-Room House | Two Bedrooms

1289 ft² (interior and deck)

Nestled amongst a wooded grove of trees, the Frasier Cottage offers private house-style accommodations. This two-bedroom, two-bathroom cottage features a kitchenette with an apartment-size refrigerator, spacious living accommodations and a gas fireplace.

Book Now
floor plan of Pridwin guest accommodations

Caroline Cottage

Multi-Room House | One Bedroom

930 ft² (interior and deck)

Private and secluded, The Caroline Cottage offers private house-style accommodations and views overlooking a wooded grove of trees. The Caroline Cottage features bedroom with a King-size bed, a separate living room with a Full-size sleeper sofa, a gas fireplace and a kitchenette with an apartment-size refrigerator.

Book Now

Now Accepting Reservations

The Pridwin is excited to open reservations for Summer 2022.
We are currently taking reservation requests for June and early July dates.
Reservations starting July 15th can be made online by clicking the link below.
Call to Request: 1 (844) 200-5001 Book Starting July 15