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