Hot Southold Cottage Rates

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Featured Cottages in Southold

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3 out of 5
690 Queen St Greenport NY
The price is AU$343 per night from 18 May to 19 May
AU$343
18 May - 19 May
includes taxes & fees
Located in Greenport, North Fork Cottages & RV Resort is within a 5-minute drive of Kontokosta Winery and Stony Brook Eastern Long Island Hospital.
Opens in a new windowNorth Fork Cottages & RV Resort
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton CT
The price is AU$314 per night from 18 May to 19 May
AU$314
18 May - 19 May
includes taxes & fees
With a stay at this cottage in Clinton, you'll be within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store Museum.
Opens in a new window1-bedroom cottage with Grove Beach 🏖️ access.
'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 NY
Located in Greenport (Pipes Cove), this cottage is within a 15-minute walk of Railroad Museum of Long Island and East End Seaport Maritime Museum.
Opens in a new window'The Gate House'on Beach front Estate with Dockage. Walk to Village .
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Fairy Tale Guest Cottage in Magic Garden by Pool

Fairy Tale Guest Cottage in Magic Garden by Pool

Bridgehampton NY
With a stay at this cottage in Bridgehampton, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and South Fork Natural History Museum and ...
Opens in a new windowFairy Tale Guest Cottage in Magic Garden by Pool
Cozy & Warm Getaway Cottage in Beach Community

Cozy & Warm Getaway Cottage in Beach Community

Niantic CT
With a stay at this cottage in Niantic, you'll be by the sea, just a 5-minute walk from Rocky Neck State Park and 14 minutes by foot from Rocky Neck State ...
Opens in a new windowCozy & Warm Getaway Cottage in Beach Community
1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.

Water Mill NY
When you stay at this cottage in Water Mill, you'll be by the sea, within a 15-minute drive of The Hamptons Beaches and Cooper's Beach.
Opens in a new window1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum.
The gardners Cottage 1 mile from long Island Sound - pet friendly

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

Clinton CT
Located in Clinton, this cottage is within a 5-minute drive of Adam Stanton House and General Store Museum and Clinton Crossing Premium Outlets.
Opens in a new windowThe gardners Cottage 1 mile from long Island Sound - pet friendly
NEW Coastal Cottage 2 Miles to Beach + Lake Access

NEW Coastal Cottage 2 Miles to Beach + Lake Access

Clinton CT
The price is AU$881 per night from 17 May to 18 May
AU$881
17 May - 18 May
includes taxes & fees
Located in Clinton, this cottage is within a 5-minute drive of Hammonasset Beach State Park and Chamard Vineyards.
Opens in a new windowNEW Coastal Cottage 2 Miles to Beach + Lake Access
Beach Cottage, private beach and pass

Beach Cottage, private beach and pass

East Lyme CT
The price is AU$915 per night from 27 May to 28 May
AU$915
27 May - 28 May
includes taxes & fees
With a stay at this cottage in Niantic, you'll be by the sea, just a 3-minute walk from McCook Point Beach and 9 minutes by foot from Childrens Museum of Southeastern ...
Opens in a new windowBeach Cottage, private beach and pass
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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
216 Cottages
Lowest Price
AU$250
Highest Price
AU$915
Popular accommodation
North Fork Cottages & RV Resort, 1-bedroom cottage with Grove Beach 🏖️ access., 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Fairy Tale Guest Cottage in Magic Garden by Pool, Cozy & Warm Getaway Cottage in Beach Community, 1940s Fisherman’s Cottage close to beach. Right next to the Water Mill museum. , The gardners Cottage 1 mile from long Island Sound - pet friendly, NEW Coastal Cottage 2 Miles to Beach + Lake Access, Beach Cottage, private beach and pass

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 AU$377 per night from 17 May to 18 May
AU$377
17 May - 18 May
includes taxes & fees
When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella ...
Opens in a new windowThe Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
The price is AU$668 per night from 17 May to 18 May
AU$668
17 May - 18 May
includes taxes & fees
With a stay at Vine & Sand in Southold, you'll be a 2-minute walk from Mattebella Vineyards and 8 minutes by foot from Corey Creek Winery.
Opens in a new windowVine & Sand
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 17 May to 18 May
AU$250
17 May - 18 May
includes taxes & fees
When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt ...
Opens in a new windowThe Bentley Hotel Southampton
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Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is AU$538 per night from 19 May to 20 May
AU$538
19 May - 20 May
includes taxes & fees
When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.
Opens in a new windowSound View Greenport
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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.

Top Picks

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^Subject to availability and chosen travel dates.