Holiday rentals with a hot tub in Sag Harbor

Walkable Designer Home in East Hampton Village!

WALK TO THE VILLAGE, BIKE TO THE BEACH from this Original East Hampton Village House! Chef Kitchen, marble countertops and High-End Appliances. Living and Dining Area w/ French Doors leading to patio and HEATED SALTWATER POOL. 3 bedrooms, 2.5 baths. Sonos sound inside and out. 2nd patio off kitchen with grill and fire pit. WALKABLE TO ALL VILLAGE SHOPS & EATS—Prada, Brunello Cucinelli, Louis Vuitton, CHANEL & more! House Keeping & Bartending Available. Inquire for Monthly & Off-Season Rental!

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

Southampton Village Newly Built Gem

Enjoy a stylish experience at this 3765+ sq ft., just built, SH Village gem! Beautiful and bright spacious home with 5 well appointed bedrooms, multiple custom closets and 5.5 baths (4 ensuite). Luxurious lighting fixtures throughout the home. Living room fireplace, vaulted wooden beam kitchen ceiling with formal dining for 10 plus. Gunite pool and spa, with multiple outdoor seating areas. Expansive media room with 75 inch TV and room length comfy cloud sofa. Two sets of washers and dryers.

Private, spacious & lovely Sag Harbor retreat

This is a lovely, very private and serene home in the woods, perfect for a quiet getaway. The deck is quite large, the furnishings are comfortable and casual. There is a lovely view of the woods from the kitchen, living room and master bedroom. We have a Gunite pool which gets tons of sunlight and there’s a hot tub on the deck, a great place to relax. (we open both in mid May and close in mid to late September) This is a very quiet neighborhood, we are on two acres and have complete privacy,

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Ranked #1 AirBNB. Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

Incredible 9+ Bed Watermill Home Wellness Retreat

Luxury 9000 SF Southampton villa with a heated gunite pool, hot tub, steam shower & sauna, 9-bedroom, 8.5-bathroom, nestled on a quiet cul-de-sac in Watermill. Bright with large windows, e-shades in bedrooms, indoor/outdoor sound system, W/D on every floor (3 sets). Formal dining/living area, chefs' kitchen, TV room, movie room, gym, outdoor kitchen, arcade, pool table, air hockey and foosball. Please read our disclosures & house manual. Not a party house and no events permitted.

1 Bedroom Apartment Sag Harbor with Pool/Hot Tub

Enjoy a relaxing experience at this charming apartment in our private home in Sag Harbor with shared use of pool and hot tub. The apartment has a separate entrance. 10 minute walk into town and bay beach. Bathroom has a shower stall no tub. Kitchen has a full refrigerator, electric cook top, toaster oven and microwave. Shared use of washer/dryer. Bath towels, sheets and beach towels included. Minimum 3 night stay. Maximum 2 people per stay. No smoking, no overnight guests.

Cozy and Updated w/ Fireplace (pool open in March)

Enjoy the festive season in Hamptons! Heated pool and hottub (open through Thanksgiving), wood-burning fireplace, renovated and well stocked kitchen and bathrooms, central A/C, new sofa (larger than that pictured), new fiber optic wifi, outdoor shower, Weber gas grill, cable/smart TVs, sonos speakers, video game consoles, ping pong table, board games, darts, books, etc. Work area with printer, monitors, and small desk. No hidden fees or burdensome cleaning/checkout requests.

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.