Hot Middletown Cottage Rates

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Featured Cottages in Middletown

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
Located in Elkton, this cottage is on the waterfront, a 5-minute drive from Chesland Park and 6 minutes from Brantwood Park.
Opens in a new windowCharming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charlestown
With a stay at this cottage in Perryville, you'll be within a 15-minute walk of Charlestown Town Hall and Fair Green Park.
Opens in a new windowCharming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
Located in Earleville, this cottage is in a rural location, within a 15-minute drive of Earleville Wildlife Management Area and Earleville Wildlife Management ...
Opens in a new windowWaterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
The price is AU$330 per night from 13 Nov to 14 Nov
AU$330
13 Nov - 14 Nov
includes taxes & fees
A stay at this cottage places you in the heart of Port Deposit, a 1-minute drive from Susquehanna River and 6 minutes from Hollywood Casino.
Opens in a new windowQuarry Landing - Center of Town & River View - 3 Bedroom
A cottage on the shore of the Delaware River

A cottage on the shore of the Delaware River

Salem
Located in Salem, this cottage is on the waterfront, a 3-minute drive from Salem River Wildlife Management Area and 10 minutes from Memorial Hospital Of Salem ...
Opens in a new windowA cottage on the shore of the Delaware River
Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view

2 out of 5
Elkton
Located in Elkton, this cottage is on the waterfront, within a 10-minute drive of Chesland Park and Brantwood Park.
Opens in a new windowSunset River Shack -amazing waterfront view
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton
With a stay at this cottage in Elkton, you'll be within a 10-minute drive of Chesland Park and Chesapeake City Bridge.
Opens in a new windowChesapeake City Pool Retreat – Waterfront Stay in the Woods
Eastern shore beachfront cottage with stunning sunset views!

Eastern shore beachfront cottage with stunning sunset views!

Worton
Located in Worton, this cottage is on the waterfront, within a 10-minute drive of Betterton Community Park and Betterton Historic District.
Opens in a new windowEastern shore beachfront cottage with stunning sunset views!
Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa

Galena
Located in Galena, this cottage is on a river, within a 10-minute drive of Galena Town Hall and Galena Town Park.
Opens in a new windowBe persuaded to experience this vintage cottage by the Sassa
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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.

Middletown 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 Middletown 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 Middletown 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 Middletown, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Middletown Cottages essential information

Accommodation
32 Cottages
Lowest Price
AU$144
Highest Price
AU$330
Popular accommodation
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC, Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Quarry Landing - Center of Town & River View - 3 Bedroom, A cottage on the shore of the Delaware River, Sunset River Shack -amazing waterfront view, Chesapeake City Pool Retreat – Waterfront Stay in the Woods, Eastern shore beachfront cottage with stunning sunset views!, Be persuaded to experience this vintage cottage by the Sassa

Top trending hotels in Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 out of 5
411 MERRIMAC AVENUE, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 11 Dec to 12 Dec
AU$183
11 Dec - 12 Dec
includes taxes & fees
Located in Middletown, Fairfield Inn & Suites by Marriott Middletown is within a 5-minute drive of Westown and Middletown Historic District.
Opens in a new windowFairfield Inn & Suites by Marriott Middletown
Hampton Inn Middletown

Hampton Inn Middletown

2.5 out of 5
117 Sandhill Dr, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 10 Dec to 11 Dec
AU$175
10 Dec - 11 Dec
includes taxes & fees
With a stay at Hampton Inn Middletown in Middletown, you'll be within a 15-minute walk of Westown and Middletown Historic District.
Opens in a new windowHampton Inn Middletown
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 out of 5
315 Auto Park Dr, Middletown, DE
Fully refundable
The price is AU$178 per night from 5 Dec to 6 Dec
AU$178
5 Dec - 6 Dec
includes taxes & fees
Located in Middletown, Holiday Inn Express & Suites Middletown by IHG is within a 5-minute drive of Dutch Country Farmers Market and Frog Hollow Golf Club.
Opens in a new windowHoliday Inn Express & Suites Middletown by IHG
Save an average of 15% on thousands of hotels when you're signed in
Pleasant Hill Motel

Pleasant Hill Motel

2.5 out of 5
3155 Dupont Pkwy, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is AU$144 per night from 12 Nov to 13 Nov
AU$144
12 Nov - 13 Nov
includes taxes & fees
With a stay at Pleasant Hill Motel in Middletown, you'll be within a 5-minute drive of Appoquinimink Friends Meeting House and Historic Houses of Odessa.
Opens in a new windowPleasant Hill Motel
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.