Guesthouse holiday rentals in The Hamptons
Find and book unique guesthouse rentals on Airbnb
Top-rated Guesthouses in The Hamptons
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for The Hamptons guesthouses
Family-Friendly guesthouses
Guesthouse in Cherry Grove, Fire Island
4.93 out of 5 average rating, 61 reviewsOne Bedroom Cottage in Cherry Grove
14–21 Sep
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
2–9 Mar
Guesthouse in East Hampton
4.9 out of 5 average rating, 187 reviewsBeautiful Airy Barn in Springs
11–18 Oct
Guesthouse in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
2–9 Oct
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
19–26 Mar
Guesthouses with a patio
Guesthouse in Shirley
4.97 out of 5 average rating, 35 reviewsLa little house J place
11–18 Jan
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
3–10 Aug
Guesthouse in Bridgehampton
4.82 out of 5 average rating, 61 reviewsCentral Hamptons Guesthouse
2–9 Jul
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 3 reviewsRetro Mid-Century Cottage 1/2 mile to CPI
10–17 Sep
Guesthouse in Hampton Bays
Hill Coast Cottage: Freshly Renovated
30 Oct – 6 Nov
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
2–9 Mar
Guesthouse in Westhampton Beach
4.79 out of 5 average rating, 14 reviewsTennis & Sea Escape
27 Oct – 3 Nov
Guesthouse in Bellport
5.0 out of 5 average rating, 9 reviewsGuest House retreat with amazing pool !!!
9–16 Oct
Guest house rentals with a washing machine and dryer
Guesthouse in Southold
4.95 out of 5 average rating, 40 reviewsSouthold- Adorable 1 Bedroom Cottage
9–16 May
Guesthouse in Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
7–14 Jun
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
27 May – 3 Jun
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
9–16 May
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
8–15 Apr
Guesthouse in Hampton Bays
5.0 out of 5 average rating, 13 reviewsOne Bedroom Hamptons Waterfront Cottage
27 Mar – 3 Apr
Guesthouse in Mount Sinai
4.67 out of 5 average rating, 6 reviewsGreat Outdoors Beach & Pool Welcome!
22–29 Oct
Guesthouse in East Quogue
4.91 out of 5 average rating, 22 reviewsHamptons Two Bedroom Cottage
31 May – 7 Jun
Destinations to explore
- New City Holiday rentals
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