Wainscott Woods Retreat Guest Houses

We selected the 914 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Wainscott Woods Retreat

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Exploring East Hampton is a breeze at this coastal cottage. Both downtown and the beach are easily accessible by bike, and a coffee shop and seafood restaurant are just down the street.

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle takes its name quite literally from the mortar and pestle collection in the dining room, a detail that represents the character and charm of this home. The many indoor and outdoor social spaces cater to groups of friends and families who love home-cooked meals and value one another's company.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.


We selected the top 3% holiday homes in Wainscott Woods Retreat Guest Houses

Explore the 914 most perfect homes in our collection

View on map

Most popular homes in Wainscott Woods Retreat

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Tucked In The Trees

Tucked In The Trees

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

A Faithful Friend

A Faithful Friend

  • 10 guests

  • 6 bedrooms

Water Mill, Southampton

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

View all

Check upcoming rates & availability for Wainscott Woods Retreat Guest Houses


Frequently asked questions

Looking for guesthouse style accommodation in Wainscott Woods Retreat? You've come to the right place: Our homes come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. Book today and enjoy a short or extended stay in the best guesthouse style accommodation that Wainscott Woods Retreat has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

Search Our Collection