Guesthouse holiday rentals in Suffolk County
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Top-rated Guesthouses in Suffolk County
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 Suffolk County guesthouses
Family-Friendly guesthouses
Guesthouse in Huntington Station
4.86 out of 5 average rating, 97 reviews2 large bedrooms in cozy little neighborhood.
4–11 Apr
Guesthouse in Sag Harbor
4.88 out of 5 average rating, 94 reviewsCharming 2BR Cottage, Walk to Town
18–25 Sep
Guesthouse in Cherry Grove, Fire Island
4.93 out of 5 average rating, 61 reviewsOne Bedroom Cottage in Cherry Grove
13–20 Sep
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
14–21 Jan
Guesthouse in East Hampton
4.9 out of 5 average rating, 187 reviewsBeautiful Airy Barn in Springs
11–18 Oct
Guesthouse in Norwalk
5.0 out of 5 average rating, 18 reviewsGuest Cottage in Rowayton
15–22 Mar
Guesthouse in Norwalk
5.0 out of 5 average rating, 58 reviewsCottage by the Sea
28 Sep – 5 Oct
Guesthouse in Westhampton
4.33 out of 5 average rating, 9 reviewsCharming Westhampton SandDollar Cottage. AC.
28 Sep – 5 Oct
Guesthouses with a patio
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
13–20 Jul
Guesthouse in Madison
4.97 out of 5 average rating, 68 reviewsBeachy & Bright Carriage House/5 min walk to Beach
16–23 Nov
Guesthouse in Wilton
5.0 out of 5 average rating, 22 reviewsThe Ciderhouse Cottage - private escape in Wilton
1–8 Aug
Guesthouse in Copiague
4.86 out of 5 average rating, 37 reviewsPalms by the bay: Waterside Cute Cozy Cottage
20–27 Aug
Guesthouse in Massapequa
5.0 out of 5 average rating, 15 reviewsModern Custom Studio: 50 mins to NYC
18–25 Jul
Guesthouse in Guilford
5.0 out of 5 average rating, 61 reviewsPage Guest House
13–20 Sep
Guesthouse in Hampton Bays
4.91 out of 5 average rating, 43 reviewsQuaint One Bedroom Cottage with Private Entrance
14–21 Aug
Guesthouse in Weston
4.96 out of 5 average rating, 25 reviewsNature Lovers Guesthouse
24–31 May
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
4–11 May
Guesthouse in East Haven
4.94 out of 5 average rating, 31 reviewsAdorable private 1-bedroom guesthouse with parking
1–8 May
Guesthouse in Huntington Station
4.98 out of 5 average rating, 66 reviewsModern fully updated 2nd Floor apartment
23 Feb – 2 Mar
Guesthouse in Southampton
4.88 out of 5 average rating, 42 reviewsModern Guesthouse
20–27 Jun
Guesthouse in Southampton
4.8 out of 5 average rating, 10 reviewsSouthampton Village Getaway
13–20 May
Guesthouse in Redding
4.97 out of 5 average rating, 30 reviewsThe Cottage in Redding
26 Nov – 3 Dec
Guesthouse in East Quogue
GuestHouse - Tennis court side luxury
22–29 May
Guesthouse in Southold
Picture perfect 2 bedroom, 1 bath private cottage
26 Feb – 5 Mar
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