Hot Southold Cottage Rates

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Featured Cottages in Southold

Adorable New England Cottage,  2 min walk to Beach 🏖️, Available year round

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Westbrook
With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Chalker Beach and Westbrook Town Beach.
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton
Located in Clinton, this cottage is within a 5-minute drive of Indian River Marina and Adam Stanton House and General Store Museum.
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Beach Bungalow, large porch, 1/2 mile to the water.

Beach Bungalow, large porch, 1/2 mile to the water.

Westbrook
The price is AU$743 per night from 30 Nov to 1 Dec
AU$743
includes taxes & fees
30 Nov - 1 Dec
With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Beach Bungalow, large porch, 1/2 mile to the water.
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Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue
When you stay at this cottage in Cutchogue, you'll be near the beach, within a 5-minute drive of Bedell Cellars and Pindar Vineyards.
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds

Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds

Old Saybrook
Located in Old Saybrook (Old Saybrook Center), this cottage is within a 5-minute drive of Connecticut River and General William Hart House.
Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds
Charming Old Saybrook Cottage < 1 Mi to Beach

Charming Old Saybrook Cottage < 1 Mi to Beach

Old Saybrook
Located in Old Saybrook, this cottage is a 4-minute drive from Connecticut River and 5 minutes from Harvey's Beach.
Charming Old Saybrook Cottage < 1 Mi to Beach
Hampton Cottage.

Hampton Cottage.

Hampton Bays
The price is AU$392 per night from 6 Nov to 7 Nov
AU$392
includes taxes & fees
6 Nov - 7 Nov
When you stay at this cottage in Hampton Bays, you'll be within a 10-minute drive of Ponquogue Beach and The Hamptons Beaches.
Hampton Cottage.
Charming Deep River Vacation Rental on Star Lake!

Charming Deep River Vacation Rental on Star Lake!

Deep River
Located in Deep River, this cottage is on a lake, a 3-minute drive from Plattwood Park and 6 minutes from Museum of Fife and Drum.
Charming Deep River Vacation Rental on Star Lake!
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

2 out of 5
Hampton Bays
Located in Hampton Bays, this cottage is by the sea, within a 15-minute drive of Ponquogue Beach and The Hamptons Beaches.
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays
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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
191 Cottages
Lowest Price
AU$136
Highest Price
AU$743
Popular accommodation
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Beach Bungalow, large porch, 1/2 mile to the water. , Totally Renovated Cottage on the North Fork 7 min. walk to the Beach, Luxury Cottage walking distance to Saybrook Point Marina, 2 King Beds, Charming Old Saybrook Cottage < 1 Mi to Beach, Hampton Cottage., Charming Deep River Vacation Rental on Star Lake!, Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

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$333 per night from 18 Nov to 19 Nov
AU$333
includes taxes & fees
18 Nov - 19 Nov
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 ...
The Shoals Suites and Slips
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$136 per night from 1 Dec to 2 Dec
AU$136
includes taxes & fees
1 Dec - 2 Dec
A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex ...
Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is AU$305 per night from 1 Dec to 2 Dec
AU$305
includes taxes & fees
1 Dec - 2 Dec
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.
Sound View Greenport
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Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3 out of 5
2038 Old Country Rd, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 26 Nov to 27 Nov
AU$177
includes taxes & fees
26 Nov - 27 Nov
A stay at Hilton Garden Inn Riverhead places you in the heart of Riverhead, within a 5-minute drive of Splish Splash Water Park and Out East Family Fun.
Hilton Garden Inn Riverhead
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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.