Hot Southold Cottage Rates

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Featured Cottages in Southold

Direct waterfront renovated cottage.

Direct waterfront renovated cottage.

Madison
Book a stay at this beach cottage in Madison. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Deacon John Grave House and Anna Mia's are located ...
Opens in a new windowDirect waterfront renovated cottage.
Fabulous Waterfront Property in the Heart of Wine Country

Fabulous Waterfront Property in the Heart of Wine Country

Peconic
Book a stay at this family-friendly cottage in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Goldsmith's Inlet Park and Sannino's ...
Opens in a new windowFabulous Waterfront Property in the Heart of Wine Country
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

greenport
Book a stay at this beach cottage in Greenport. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Railroad Museum of Long Island and East ...
Opens in a new window'The Gate House'on Beach front Estate with Dockage. Walk to Village .
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1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
The price is NZ$321 per night from 29 Sept to 30 Sept
NZ$321
29 Sept - 30 Sept
includes taxes & fees
Stay at this cottage in Clinton. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Clinton Plaza Shopping Center ...
Opens in a new window1-bedroom cottage with Grove Beach 🏖️ access.
Sweet Cottage in Beach Community

Sweet Cottage in Beach Community

Niantic
Stay at this cottage in Niantic. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Giants Neck Beach and Rocky Neck State Park are located ...
Opens in a new windowSweet Cottage in Beach Community
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton
Book a stay at this family-friendly cottage in Clinton. Enjoy a garden, laundry facilities, and patios. Popular attractions Indian River Marina and Adam Stanton ...
Opens in a new windowCozy cottage near downtown Clinton, Marina & Hammonasset Park
The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton
Stay at this cottage in Clinton. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Adam Stanton House and General Store Museum ...
Opens in a new windowThe gardners Cottage 1 mile from long Island Sound - pet friendly
Southampton cozy cottage by the beach

Southampton cozy cottage by the beach

Hampton Bays
Stay at this vacation home in Hampton Bays. Enjoy free WiFi and air conditioning. Popular attractions Cooper's Beach and Meschutt Beach are located nearby.
Opens in a new windowSouthampton cozy cottage by the beach
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Calverton
Book a stay at this beach cottage in Calverton. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Splish Splash Water Park and Baiting ...
Opens in a new windowRenovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Southold Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Southold will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Southold definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Southold, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Southold Cottages essential information

Accommodation
198 Cottages
Lowest Price
NZ$160
Highest Price
NZ$743
Popular accommodation
Direct waterfront renovated cottage. , Fabulous Waterfront Property in the Heart of Wine Country, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., 1-bedroom cottage with Grove Beach 🏖️ access., Sweet Cottage in Beach Community, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, The gardners Cottage 1 mile from long Island Sound - pet friendly, Southampton cozy cottage by the beach, Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Top trending hotels in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is NZ$519 per night from 28 Sept to 29 Sept
NZ$519
28 Sept - 29 Sept
includes taxes & fees
Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowThe Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$160 per night from 28 Sept to 29 Sept
NZ$160
28 Sept - 29 Sept
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowPier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NZ$577 per night from 27 Oct to 28 Oct
NZ$577
27 Oct - 28 Oct
includes taxes & fees
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowSound View Greenport
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Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NZ$743 per night from 14 Oct to 15 Oct
NZ$743
14 Oct - 15 Oct
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
Opens in a new windowSaybrook Point Resort & Marina
Don't see what you're looking for?
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.