
Holiday rentals with breakfast in Southampton
Find and book unique Holiday Accommodation with Breakfast on Airbnb
Quick stats about holiday rentals with breakfast included in Southampton

Total holiday rentals
Explore 20 holiday rentals in Southampton

Nightly prices starting at
Southampton holiday rentals start at $319 AUD per night before taxes and fees

Verified guest reviews
Over 600 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Southampton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Southampton rentals

4.9 Average rating
Southampton stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Holiday Accommodation with Breakfast in Southampton
Guests agree: These breakfast rentals are highly rated for location, cleanliness and more.

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.

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!

Chic, Modern, Family-Friendly Home in East Hampton
This clean, beautiful, well appointed home is the perfect place for your summer (or winter) getaway! With updated appliances and designer furniture, this chic getaway is both fun and sophisticated. Whether you're a family or a small group of friends, you will make wonderful memories swimming in the heated gunite pool, playing badminton in the yard, grilling on the deck or sipping wine on the balcony. Close to the village, and both bay and ocean beaches! Rental Registry Certificate: RR-25-371

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.

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

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

2Br Hampton Family Escape: Beaches, kayaks, BBQ
Holiday Retreat ready for you and your family to enjoy. Welcome to our charming 2BR, 1BA Hampton's Retreat apt. in Hampton Bays, NY! Your stay offers a bright, airy space with a large screen TV, board games, and a private work area. The split-unit AC/heating ensures comfort w/ a fenced back yard with BBQ for your family’s pleasure. Just 1 mile from the bay beach. 2 miles from the ocean beaches , and only 1.5 miles to the town’s shops, dining, and local happenings.

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!

Secluded Farmhouse - Studio Apartment Style Unit
Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

The Villager
This is a newly renovated studio apartment located in the Village of Patchogue. Walking distance to numerous restaurants, breweries, sports bars and shops. Walking distance to the Long Island Railroad with service to NYC, The Hamptons, Wine Country and Montauk. We are close to the Fire Island Ferries, beaches and parks.

Blissful Bridgehampton
If you want to heat the pool, there will be an extra charge. Very private that sits back on a preserve. 20 by 40 gunite pool. Close to the Hampton Classic. 15 minutes to East Hampton, 10 min Southampton. Bridgehampton and Sag Harbor Town is 5 to 7 minutes away.

SLEEK, RENOVATED SHELTER ISLAND GEM
Enjoy your summer at this fresh and inviting completely renovated 3 bedroom, 4 bath home on 1.12 acres. Some of the many highlights are a sunny open layout including living room with elevated ceilings, dining area with ...... (continued below)...
Popular amenities for Southampton Holiday Accommodation with Breakfast
Holiday House Rentals with breakfast

Fire Island Pines Beach House - Oceanfront Bedroom

The Bay & Vine Retreat

RENOVATED AND SPACIOUS SUMMER HOME WITH WATER VIEW

Private floor with views of Shinnecock Bay!

Gorgeous Renovated Bellport Village home w/ Gym

Sag Harbor Beach Cottage

No place like home

Private 2 Bedrooms 1 Bath in East Hampton
Apartment rentals with breakfast

A beautiful 2 BR apt near beach W/hot tube

Queen room with ensuite bathroom

A 1 BR Luxury Apt to relax w/hot tube

2Br Hampton Family Escape: Beaches, kayaks, BBQ

The Villager
Bed and breakfast rentals with breakfast

SEVEN on Shelter - Queen Guest Room

Village ~ Summer Classic Southampton Private Room

Vine + Sand Southold, NY's Newest B&B-Room 2

Southampton Center ~ Light & Airy Private Room

Head of Pond House - The Mill Pond Suite

Cottage King, Water Views, Beaches/Golf/Vineyard

2BedKitchenette Water Views, Beaches/Golf/Vineyard

Head of Pond House- Edge of Woods Room
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- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Robert Moses State Park Beach
- Southampton Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Yale University Art Gallery
- Long Island Aquarium
- Wölffer Estate Vineyard
- Meschutt Beach
- Orient Beach State Park
- Blue Shutters Beach
- Soundview Beach
- Wesleyan University
- Ocean Beach
- Dunewood





