Vacation rentals with breakfast in Southampton

The Red Cottage Circa 1936

This cottage is a gem to be found! From the primary room to the charming loft, this cottage can sleep 6! There is a full working kitchen. For those who wish to do exploring, you will be centrally located on LI giving you great ease in using LI rail road (.5 mile) from cottage and Port Jeff Ferry (1mile)from cottage. There is a large fenced in yard with BBQ and outdoor seating if you wish to dine in. Dogs are allowed w/prior notice and a $65 pet fee per dog. You won’t beat this value reserve now.

Location · Value · Breakfast

NEW: Charming East Hampton home w/ POOL!

Welcome to our charming 3 bedroom, 2.5 bath, 1,700+ SF home. Enjoy the heated pool all summer or relax by the fireplace in the fall and winter months. Sunlight shines through two skylights and oversized windows for the beautiful natural light that East Hampton Springs are famous for. We are just a few minutes drive to all EH bay and ocean beaches as well as EH Town and Amagansett Village. Countless restaurants, shops, farmer's markets, vineyards, art galleries, etc. are all very close by!

Location · Family · Quiet

A Cheerful 2 - Bedroom Cottage

The cottage is the perfect resting spot for travelers. While staying here you can enjoy nature, farms, vinyards, beaches, golfing, and local attractions. We are conveniently located between the North and South Forks of Long Island. We are in walking distance to the Hampton's Jitney. A 2 min drive to the LIE. And just a 40 min drive to the Orient Pt Ferry. We are 30 mins to The Hamptons, and 5 mins to the LIRR. Most importantly we can assure your stay with us will be, peaceful and comfortable.

Family · Location · Decor

POOL + Beach Oasis! Winter deals 2+ nights!

Chef kitchen: 2 ovens/lux app's/coffee bar w/ Nespresso/Keurig 2 living rooms Dining room seats 10 1st floor Primary Suite: king bed, gas fireplace, furnished deck overlooking pool, 4 piece bath: huge shower & jacuzzi tub 2 of 4 Guest rooms on 1st fl Gym/yoga rm: bench + weights (no treadmill) TV's in bedrooms inc. Firesticks Fenced backyard oasis w/ heated mineral spring pool, loungers, shaded cabana, outdoor dining, & Weber BBQ, outdoor shower Kitchenette in den/office Central AC/heat/fans

Family · Location · Cleanliness

Beautiful Hampton Home, 4 bedroom, heated pool

Beautiful Hampton 4 bedroom, 3 1/2 bath home, with heated pool, outdoor shower, located on one acre,in beautiful upscale neighborhood ,located on quiet cul-da-sac street.Close to Sag Harbor town and beaches. Large 65" TV in huge Cathedral main living room. 65" TV also in large separate den with treadmill. King Size bed on 1St floor with 2 beds next door. New large Spa bathroom on 1st floor. King Size Master bedroom 2nd floor,50"TV ,and en-suite bathroom. 2 beds in add bedroom, with en-suite

Family · Location · Kitchen

Modern Hamptons Home

Escape to a beautifully renovated Hamptons retreat designed for comfort, privacy, and effortless outdoor living. Enjoy a spacious deck and private fenced backyard featuring a unique outdoor lounge, BBQ grill, fire pit, and refreshing outdoor shower. Inside, bright and stylish spaces offer all the comforts of home. Perfect for relaxing, dining outdoors, and creating memorable moments with family and friends, all while being conveniently located near beaches, restaurants, shopping, and local.

Location · Value · Sleep quality

A beautiful 2 BR apt near beach W/hot tube

✨ Luxury Family Retreat | Modern Comfort Near Beach & City ✨ Welcome to your home away from home! This modern, family-friendly getaway is designed for total relaxation and convenience. Enjoy an open floor plan, stylish décor, and all the comforts you need for a peaceful stay. 🏖 6-minute drive to the beach 🚆 3 minutes to the train station 🌇 Close to city attractions 🌿 Quiet suburban neighborhood Come unwind, connect, and recharge — you’ll feel right at home the moment you arrive.

Family · Location · Nearby

Beach home waterfront LI amazing view 3/3 bed bath

Beach front home with spa/ PRIVATE BEACH , Water park, wineries, aquarium & ocean within20 min. Granite covered barbecue, wet bar and 55” TV . Fire pit, comfortable seating while watching sunrise or sunset from your overlook onto LI SOUND. 3 bedroom , 3 full bathroom with 2 queen beds and 1 king. Enjoy spectacular views from the windows with cozy relaxed living and dining areas. Day trip to Hamptons, Montauk all attractions and highways. Hiking trails , parks and recreation.

Location · Family · Sleep quality

The Buccaneer Suite ~ Your Private Seaside Escape

Come be enchanted with The Buccaneer, a private, luxurious yet charming two-bedroom duplex suite nestled within Falaena House Inn - our historic, eco-conscious retreat. Blending coastal elegance with maritime spirit, The Buccaneer offers a rare sense of seclusion while placing you a mere two-minute stroll to the beach, local shops & coastal eateries. At Falaena House Inn, we care deeply for the land, the sea, and you! We welcome you home like a captain to port (adult-only, no-pets).

Location · Family · Indoor spaces

Summer Cottage

Cottage in Roses Groves, Southampton, NY. Great location to avoid traffic on 27. Cottage has access to a private beach on the Peconic Bay (5 min walk). 15 min drive to ocean beaches in Southampton, and Southampton village. 10 min drive to Watermill, 20 min to Sag Harbor and BH. A farm and a deli are less than a mile away. Two restaurants nearby Perfect for artists, ocean lovers, book lovers and families. A/C in living room and bedrooms. Located on a quiet street, very relaxing

Family · Value · Biking

Artists pet friendly apartment and cabin, sauna.

Full apartment with full bathroom 10 minutes to all Hampton towns. Quiet property Walking distance to free SUP boards and canoes and only 2 minute drive to a dog friendly beaches. Extra bedroom is a Cabin in the middle of the property and was a recording studio, now has queen bed, wifi, fridge, micro wave, heat and AC, TV and DVD player but no bathroom. You have your own parking spots, entrance and outdoor dining area and outdoor shower.

Location · Accuracy · Backyard

The Bay & Vine Retreat

Escape to Southold in the heart of North Fork wine country. Steps from vineyards, the bay, and a private beach, this luxury retreat features an heated pool, private dock access, and spacious indoor/outdoor living. Minutes to local farms, seafood markets, water sports, top restaurants, and the charming waterfront village of Greenport — perfect for relaxing coastal getaways year-round.

Family · Location · Beach