Guesthouse holiday rentals in Fire Island

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Top-rated Guesthouses in Fire Island

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Oyster Bay

4.96 out of 5 average rating, 179 reviews

GORGEOUS & SERENE in Oyster Bay - LI/NY

Our small, modern bungalow is completely private. Perfect for working as it is for a romance, or just coming to LI-NY for the weekend. The luxurious queen bed is great, alone, or shared, and the custom sofa converts into another bed or two in a pinch (ask us about this before booking, it's got its limits); keep in mind that this is an open loft-like space. We're located on Long Island's North Shore, close to beaches yet only 45-minutes from Manhattan, and less than an-hour to The Hampton's.

17–24 Nov

$485 NZD per night

Guest favourite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Escape the city, work in nature! Totally private cottage with garden views , central air and heated floors. 1 mile from pristine beaches and center of town, LIRR, Hampton Jitney, 3 large grocery stores, Starbucks, organic market, shopping & restaurants. King bed, cable TV, refrigerator w/ice, microwave, outdoor grill, private yard, Perfect for couples, solo, 1-2 small kids. We welcome small dogs for a $100 fee. Please message us with the size and type. Working couple/owners in main house.

5–12 May

$622 NZD per night

Guest favourite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

21–28 Sep

$612 NZD per night

Guest favourite

Guesthouse in Norwalk

4.99 out of 5 average rating, 209 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

3–10 Nov

$247 NZD per night

Guest favourite

Guesthouse in Norwalk

5.0 out of 5 average rating, 113 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

11–16 Jul

$678 NZD per night

Guest favourite

Guesthouse in New Haven

4.94 out of 5 average rating, 240 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

22–29 Aug

$404 NZD per night

Guest favourite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

23–30 Oct

$241 NZD per night

Guest favourite

Guesthouse in Brookhaven

4.97 out of 5 average rating, 215 reviews

The Unhampton

This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

20–27 Mar

$294 NZD per night

Guest favourite

Guesthouse in Guilford

4.99 out of 5 average rating, 454 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING BIRDS HAVE ARRIVED. Spring is here!!. Beautiful days and nights. Hike on the trails. Bike along the ocean. Cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

12–19 Jun

$565 NZD per night

Guest favourite

Guesthouse in Brewster

5.0 out of 5 average rating, 290 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

14–21 Sep

$380 NZD per night

Guest favourite

Guesthouse in Sayville

4.97 out of 5 average rating, 183 reviews

Great South Bay Cottage

Fantastic private cottage on Long Island's South Shore. Great access to the best beaches in the world (walk to bay, ferries to ocean). Short train ride to/from NYC, Wineries & The Hampton's. Experience the Island’s charm and culture. Enjoy Long Island summers. We are COVID conscious and employ a professional cleaning regiment.

28 Jan – 4 Feb

$354 NZD per night

Guest favourite

Guesthouse in Bedford

4.92 out of 5 average rating, 173 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

19–26 Sep

$315 NZD per night