Subscribe to Guide
No Result
View All Result
Hamptons.com
  • Spotlight Magazine
  • Lifestyle
    • Featured
    • Entertainment
    • Arts
    • Community
    • Dining
    • Recreation
    • Trending
  • Guides
  • Events
    • Events Calendar
    • Post an Event
    • Gallery
  • Real Estate
    • Real Estate Features
    • Hamptons Real Estate Market Data
    • Search Hamptons Real Estate
      • Open Houses
      • Search Sales
      • Search Rentals
    • Search South Florida Real Estate
    • Title Insurance
    • Happening In The Hamptons Podcast
  • Live Cameras
    • All Live Cameras
    • Live Weather Cams
    • Amagansett, Atlantic Avenue Beach
    • Bridgehampton, West Scott Cameron Beach
    • East Hampton Village, Main Beach
    • East Hampton Village, Main Street
    • East Hampton Village, Newtown Lane
    • Hampton Bays, Ponquogue Beach
    • Hampton Bays, Ponquogue Bridge
    • Hampton Bays, Shinnecock Fishing Dock
    • Hampton Bays, Tiana Beach
    • Long Island Aquarium | Coral Reef
    • Long Island Aquarium | Penguins
    • Long Island Aquarium | Shark Tank
    • Montauk, Downtown Circle
    • Montauk, Lars Simenson Skatepark
    • Montauk, Gin Beach & Inlet
    • Montauk, Sunset Beach & Inlet
    • Sagaponack, Sagg Main Beach
    • Sag Harbor, Bay Street
    • Sag Harbor, Foster Memorial Beach
    • Sag Harbor, Long Wharf Marina
    • Sag Harbor, Sag Harbor Bay
    • Sag Harbor, Windmill Beach & Bay
    • Shelter Island, South Ferry
    • Southampton, 39A to Montauk Hwy Merge
    • Southampton, Conscience Point Marina
    • Southampton Village, Coopers Beach
    • Southampton Village, Main Street (North)
    • Southampton Village, Main Street (Hildreths)
    • Westhampton, Pike’s Beach
    • Westhampton Village, Main Street (East)
    • Westhampton Village, Rogers Beach
  • Public WiFi
    • Public WiFi Map
    • Public Wi-Fi Support
  • Spotlight Magazine
  • Lifestyle
    • Featured
    • Entertainment
    • Arts
    • Community
    • Dining
    • Recreation
    • Trending
  • Guides
  • Events
    • Events Calendar
    • Post an Event
    • Gallery
  • Real Estate
    • Real Estate Features
    • Hamptons Real Estate Market Data
    • Search Hamptons Real Estate
      • Open Houses
      • Search Sales
      • Search Rentals
    • Search South Florida Real Estate
    • Title Insurance
    • Happening In The Hamptons Podcast
  • Live Cameras
    • All Live Cameras
    • Live Weather Cams
    • Amagansett, Atlantic Avenue Beach
    • Bridgehampton, West Scott Cameron Beach
    • East Hampton Village, Main Beach
    • East Hampton Village, Main Street
    • East Hampton Village, Newtown Lane
    • Hampton Bays, Ponquogue Beach
    • Hampton Bays, Ponquogue Bridge
    • Hampton Bays, Shinnecock Fishing Dock
    • Hampton Bays, Tiana Beach
    • Long Island Aquarium | Coral Reef
    • Long Island Aquarium | Penguins
    • Long Island Aquarium | Shark Tank
    • Montauk, Downtown Circle
    • Montauk, Lars Simenson Skatepark
    • Montauk, Gin Beach & Inlet
    • Montauk, Sunset Beach & Inlet
    • Sagaponack, Sagg Main Beach
    • Sag Harbor, Bay Street
    • Sag Harbor, Foster Memorial Beach
    • Sag Harbor, Long Wharf Marina
    • Sag Harbor, Sag Harbor Bay
    • Sag Harbor, Windmill Beach & Bay
    • Shelter Island, South Ferry
    • Southampton, 39A to Montauk Hwy Merge
    • Southampton, Conscience Point Marina
    • Southampton Village, Coopers Beach
    • Southampton Village, Main Street (North)
    • Southampton Village, Main Street (Hildreths)
    • Westhampton, Pike’s Beach
    • Westhampton Village, Main Street (East)
    • Westhampton Village, Rogers Beach
  • Public WiFi
    • Public WiFi Map
    • Public Wi-Fi Support
No Result
View All Result
Hamptons.com
February 3, 2015

To Buy Or Not To Buy A Vacation Home?

18
VIEWS
Rocco A. Carrieroby Rocco A. Carriero
in Real Estate
Home Real Estate

You’ve always wanted to own a vacation home, and now you finally feel ready to make that purchase. Before you put an offer in for a cabin on the lake or condo in the mountains, consider the realities of owning a second property. Here are a few questions to think about before you finalize your plans.

Can you afford it?

Owning a second home entails additional expenses such as:

  • Furniture or other household items
  • Travel costs like airfare or wear and tear on your vehicle
  • Annual repairs or improvements to the property
  • Recreational desires such as a boat, winter skis or kayaks
  • Utilities including heat, air conditioning, water, internet and cable if you choose to have it
  • A security system for when you’re away

    If your primary residence is more than a few hours away from your vacation home, or if you plan to rent out your vacation home, you also may need to hire someone to manage the property.

    Is the location right?

    Naturally, you have an idea of where you’d like your vacation home to be located. But, have you given much thought to what that means in terms of year-round use? Homes in areas where temperatures dip below freezing need to be winterized and monitored to avoid frozen pipes. Where there’s snowfall, there’s shoveling and plowing to manage. Distance is also a key consideration, along with the relative ease of getting there. Have you chosen a location and property that will grow in value or will it be hard to sell when the time comes? These are all important questions to answer as you consider purchasing another home.

    Would renting be a better option?

    You don’t have to buy a vacation home to get away on a regular basis. A short-term rental property can provide the comforts of a home without the obligations of ownership. Rather than be tied to one place, you can try new locations and accommodations when you take a vacation. You can search online for everything from barebones apartments to sprawling homes, with rental options by the day, week or month. Alternately, if you do move forward with the purchase of a vacation home, you may want to explore listing your property as a rental when it’s not in use. If your vacation home is in a high demand area, you might be able to generate an income stream — but don’t forget to factor in the costs of managing the property from afar.

    How will your taxes be affected?

    Different tax rules apply to owning a second home, which can be somewhat complex depending on a variety of factors. Whether or not you rent the home, property taxes and mortgage interest are a few items that could affect your tax return. You’ll want to consult with a tax advisor to sort out the details and discuss how your taxes will be affected if you purchase another home.

    There are a lot of factors to think about before purchasing a vacation home. Consider working with a financial professional to determine how buying a second home will affect your longer-term financial plan.

  • STAY UPDATED

    Sign up for our weekly newsletter!

    Get the top Hamptons events and latest scoop!

    TRENDING

    Sag Harbor just got a little more stylish. Madewell opened the doors to its newest women's store at 102 Main Street, and the celebration weekend that followed felt less like a typical retail opening and more like the whole village had been invited to a party.

    New to Sag Harbor, Madewell Is Already Giving Back to the Community

    Sag Harbor just got a little more stylish. Madewell opened the doors to its newest women’s store at 102 Main Street, and the celebration weekend that followed felt less like a typical retail opening and more like the whole village had been invited to a party.

    Read more
    Since launching New York Pilates in 2013, co-founder Heather Andersen has helped redefine the modern Pilates experience, bringing a fresh, high-energy approach to a method she had been teaching and refining for years. With a deep understanding of the practice and a commitment to form-focused, intentional movement, Heather has built a brand that makes Pilates both accessible and effective for all levels.

    From First Class to Next Level: Heather Andersen’s Top Pilates Tips

    Since launching New York Pilates in 2013, co-founder Heather Andersen has helped redefine the modern Pilates experience, bringing a fresh, high-energy approach to a method she had been teaching and refining for years. With a deep understanding of the practice and a commitment to form-focused, intentional movement, Heather has built a brand that makes Pilates both accessible and effective for all levels.

    Read more
    In a Hamptons market where inventory remains historically tight, land has taken on a different kind of importance. We all know the adage, “they’re not making any more of it.” And, as far as land listings are concerned, the recently listed parcel at 20 Fieldview Lane, represented by Romaine Gordon and Sarah Minardi, just outside East Hampton Village, is almost unheard of.

    An East Hampton Opportunity That Could Not Be Recreated Today

    In a Hamptons market where inventory remains historically tight, land has taken on a different kind of importance. We all know the adage, “they’re not making any more of it.” And, as far as land listings are concerned, the recently listed parcel at 20 Fieldview Lane, represented by Romaine Gordon and Sarah Minardi, just outside East Hampton Village, is almost unheard of.

    Read more

    Search Articles

    No Result
    View All Result

    Events

        Life & Figure Drawing with Bruce Lieberman
        Life & Figure Drawing with Bruce Lieberman
        1 Jul 26
        Bridgehampton
        Ralph’s Coffee at Mulford Farm
        Ralph’s Coffee at Mulford Farm
        2 Jul 26
        East Hampton
        Stuart Weitzman Pop-Up
        Stuart Weitzman Pop-Up
        2 Jul 26
        East Hampton
        Story Time at Madoo
        Story Time at Madoo
        6 Jul 26
        Bridgehampton
        Learn To Draw What You See: Adult Drawing
        Learn To Draw What You See: Adult Drawing
        7 Jul 26
        Wainscott

    Hamptons Surf Report

    Next Post
    The Jam Session Makes A Big Move For February Performances

    The Jam Session Makes A Big Move For February Performances

    • It’s Fourth of July Weekend! ⁠
⁠
Check out our guide to all the fireworks displays set to dazzle the Hamptons. ✨⁠

⁠
🎇 Stars Over Montauk Fireworks by Grucci⁠
📅 Saturday, July 4 | 9 PM⁠
📍 Best viewing from Gosman’s Dock & Gin Beach, Montauk⁠
Bring a blanket or beach chair and enjoy one of the East End’s most spectacular fireworks shows.⁠
⁠
🚢 Fourth of July Fireworks Cruise aboard the Viking Classic⁠
📅 Saturday, July 4 | 8 PM⁠
📍 Viking Fishing Fleet, Montauk⁠
Watch the fireworks from the water while enjoying a cocktail hour and live music from The Realm Band.⁠
⁠
🎆 Devon Yacht Club Fireworks⁠
📅 Friday, July 3 | 9:15 PM⁠
📍 View from Fresh Pond Beach, Amagansett⁠
Although the event is private, the fireworks can be enjoyed from nearby Fresh Pond Beach.⁠
⁠
🎇 East Hampton Fire Department Fireworks⁠
📅 Saturday, July 4 | At Dark⁠
📍 Main Beach, East Hampton⁠
A beloved annual tradition lighting up the skies over Main Beach.⁠
⁠
🎆 Westhampton Country Club Fireworks⁠
📅 Saturday, July 4 | 9 PM⁠
📍 Westhampton⁠
While hosted by the country club, spectators gather throughout the village for great views of the Grucci fireworks.⁠
⁠
🎡 North Sea Fire Department Carnival Fireworks⁠
📅 Thursday, July 2 & Saturday, July 4 | At Dark⁠
📍 Firemen’s Field, Southampton⁠
Enjoy carnival rides, games, food, and two nights of fireworks.⁠
⁠
🎇 Sag Harbor Yacht Club John A. Ward Fireworks⁠
📅 Saturday, July 4 | 9:30 PM⁠
📍 Marine Park, Sag Harbor⁠
Don’t forget to tune into WLNG 92.1 FM for the synchronized fireworks soundtrack!⁠
⁠
✨ The Clamshell Foundation Fireworks Over Three Mile Harbor⁠
📅 Saturday, July 11 | 9 PM⁠
📍 Three Mile Harbor, East Hampton⁠
Keep the celebration going with this annual summertime fireworks display.⁠
⁠
🎆 Shelter Island Fireworks Spectacular⁠
📅 Saturday, July 11 | 9 PM⁠
📍 Crescent Beach, Shelter Island Heights⁠
A favorite community tradition overlooking beautiful Crescent Beach.⁠
⁠
#fourthofjuly #hamptons #fireworks #montauk
    • There are some restaurants in the Hamptons that simply become institutions, and Pierre’s in Bridgehampton is undoubtedly one of them.

One of the restaurant’s most famous dishes is its legendary chicken entrée, served with perfectly prepared vegetables and creamy mashed potatoes. It’s the kind of dish that keeps people coming back again and again for lunch. Chicken is one of the hardest dishes to make in my opinion, especially if it’s not fried, and this one is flawlessly executed every single time.

 #pierres #hamptons #bridgehampton #dining #review
    • Sean’s Place has been one of those beloved local institutions for years, and after this morning’s visit, it’s easy to understand why. Before I even walked inside, there was a line stretching out the door. In the Hamptons, where new restaurants seem to pop up every season, that kind of loyalty says everything.

 #hamptons #seansplace #breakfast #eggsandwich
    • Tour beautiful houses all summer long with Saunders Associates every Thursday and Friday this summer. Check @hamptonsrealestate for updates on the locations of the house houses. 

 @hamptoncoffee 
#Coffee #openhouse #summer
    • Top Hamptons Events This Weekend:⁠
⁠
🎤 Snoop Dogg at The Surf Lodge⁠
📅 Saturday, July 4 | 4 PM⁠
📍 The Surf Lodge, Montauk⁠
Kick off your holiday weekend with sunset views, cocktails, and a live performance from Snoop Dogg.⁠
⁠
🇺🇸 Southampton Independence Day Parade⁠
📅 Saturday, July 4 | 10 AM – 12 PM⁠
📍 Railroad Plaza, Southampton⁠
Celebrate Independence Day at one of the Hamptons’ favorite holiday traditions.⁠
⁠
🍸 Bar Rêve Residency at Canoe Place Inn⁠
📅 July 7–12 | From 5 PM⁠
📍 Canoe Place Inn, Hampton Bays⁠
Enjoy a taste of France with signature cocktails inspired by the season.⁠
⁠
👠 Stuart Weitzman Pop-Up⁠
📅 July 3–31 | 11 AM – 7 PM⁠
📍 The Maidstone, East Hampton⁠
Shop the Summer 2026 collection featuring statement sandals, wedges, flats, men’s footwear, and more.⁠
⁠
🛍️ GUIZIO × ESSX × Montauk General Pop-Up⁠
📅 July 3–5 | 11 AM – 6 PM⁠
📍 ESSX, East Hampton⁠
Browse the latest GUIZIO collection and grab complimentary matcha from Montauk General for the first 50 visitors each day.⁠
⁠
🌅 Chelsea After Dark × Gurney’s⁠
📅 Sunday, July 5 | 6 PM⁠
📍 Gurney’s Montauk⁠
Enjoy beachfront DJ sets from Piper Phillips, Oli Benz, and Mark Wolf as the sun goes down.⁠
⁠
✨ Glacē™ by Candela at The HUB⁠
📅 July 3–6⁠
📍 The HUB, Bridgehampton⁠
Experience complimentary personalized Glacē™ facial treatments for glowing summer skin.⁠
⁠
☕ Ralph’s Coffee at Mulford Farm⁠
📅 Now through September 7 | 8 AM – 5 PM⁠
📍 Mulford Farm, East Hampton⁠
Grab a coffee and a pastry while enjoying one of the Hamptons’ most picturesque settings.⁠
⁠
🎨 Bridgehampton Art Affair⁠
📅 July 3–5 | 10 AM – 6 PM⁠
📍 Bridgehampton Museum – Corwith House⁠
Discover local artists and browse an incredible collection of fine art.⁠
⁠
🖼️ The Cadence of Form Exhibition⁠
📅 Friday, July 3 | 5 PM – 7 PM⁠
📍 C Fine Art + Advisory / Sculpture Sights, Shelter Island⁠
Explore an exhibition celebrating abstraction through form, movement, and material.⁠
⁠
🇺🇸 Which event are you checking out this weekend?⁠
⁠
#hamptons #montauk #fourthofjuly #ralphscoffee #popup
    • GUIZIO x ESSX x Montauk General Pop-Up
 
When: Fri, July 3rd – Sun, July 5th, 2026
11am – 6pm

Where: ESSX, 53 The Circle,
East Hampton, NY

NYC-based fashion label GUIZIO will be popping up at ESSX East Hampton, bringing a curated assortment of the brand’s latest arrivals and bestselling styles to the Hamptons 
 
#guizio #essx #hamptons #easthampton #popup
    Instagram Youtube TikTok Twitter
    Hamptons.com

    Saunders Broadcasting Corp.

    Phone: 631-613-8440
    Email: [email protected]
    Facebook: Facebook.com/HamptonsOnline
    Twitter: @Hamptons
    Instagram: @HamptonsOnline

    About Us | Contact Us

    Hamptons.com

    • Lifestyle
    • Events
    • Real Estate
    • Live Cameras
    • Public WiFi

    Subscribe

    Sign up for our weekly newsletter!

    Get the top Hamptons events and latest scoop!

    © 2025 Hamptons.com | All rights reserved
    Saunders Broadcasting Corp.
    Terms & Conditions | Privacy Policy | About Us | Contact Us

     

    Sign up for our weekly newsletter!

    Get the top Hamptons events and latest scoop!

    No Result
    View All Result
    • Spotlight Magazine
    • Lifestyle
      • Featured
      • Entertainment
      • Arts
      • Community
      • Dining
      • Recreation
      • Trending
    • Guides
    • Events
      • Events Calendar
      • Post an Event
      • Gallery
    • Real Estate
      • Real Estate Features
      • Hamptons Real Estate Market Data
      • Search Hamptons Real Estate
        • Open Houses
        • Search Sales
        • Search Rentals
      • Search South Florida Real Estate
      • Title Insurance
      • Happening In The Hamptons Podcast
    • Live Cameras
      • All Live Cameras
      • Live Weather Cams
      • Amagansett, Atlantic Avenue Beach
      • Bridgehampton, West Scott Cameron Beach
      • East Hampton Village, Main Beach
      • East Hampton Village, Main Street
      • East Hampton Village, Newtown Lane
      • Hampton Bays, Ponquogue Beach
      • Hampton Bays, Ponquogue Bridge
      • Hampton Bays, Shinnecock Fishing Dock
      • Hampton Bays, Tiana Beach
      • Long Island Aquarium | Coral Reef
      • Long Island Aquarium | Penguins
      • Long Island Aquarium | Shark Tank
      • Montauk, Downtown Circle
      • Montauk, Lars Simenson Skatepark
      • Montauk, Gin Beach & Inlet
      • Montauk, Sunset Beach & Inlet
      • Sagaponack, Sagg Main Beach
      • Sag Harbor, Bay Street
      • Sag Harbor, Foster Memorial Beach
      • Sag Harbor, Long Wharf Marina
      • Sag Harbor, Sag Harbor Bay
      • Sag Harbor, Windmill Beach & Bay
      • Shelter Island, South Ferry
      • Southampton, 39A to Montauk Hwy Merge
      • Southampton, Conscience Point Marina
      • Southampton Village, Coopers Beach
      • Southampton Village, Main Street (North)
      • Southampton Village, Main Street (Hildreths)
      • Westhampton, Pike’s Beach
      • Westhampton Village, Main Street (East)
      • Westhampton Village, Rogers Beach
    • Public WiFi
      • Public WiFi Map
      • Public Wi-Fi Support

    © 2025 Hamptons.com | All rights reserved
    Saunders Broadcasting Corp.
    Terms & Conditions | Privacy Policy | About Us | Contact Us