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

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

Port Deposit MD
The price is AU$316 per night from 17 Feb to 18 Feb
AU$316
17 Feb - 18 Feb
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
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton MD
With a stay at this cottage in Elkton, you'll be within a 10-minute drive of Chesland Park and Brantwood Park.
Opens in a new windowChesapeake City Pool Retreat – Waterfront Stay in the Woods
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Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD
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
Eastern shore beachfront cottage with stunning sunset views!

Eastern shore beachfront cottage with stunning sunset views!

Worton MD
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 MD
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
Walk to Town & River: Charming Home in North East!

Walk to Town & River: Charming Home in North East!

3 out of 5
North East MD
With a stay at this cottage in North East, you'll be within a 10-minute drive of Milburn Stone Theater and Charlestown Town Hall.
Opens in a new windowWalk to Town & River: Charming Home in North East!
Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!

Chesapeake City MD
When you stay at this cottage in Chesapeake City, you'll be on the waterfront, just steps from Chesapeake Inn Marina and Chesapeake City Town Hall.
Opens in a new windowWaterfront Cottage on the C&D Canal!
Charming 2-bedroom water oriented cottage with water access

Charming 2-bedroom water oriented cottage with water access

North East MD
Located in North East, this cottage is on a river, a 4-minute drive from Upper Bay Museum and 9 minutes from Roachs Shore.
Opens in a new windowCharming 2-bedroom water oriented cottage with water access
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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
27 Cottages
Lowest Price
AU$124
Highest Price
AU$316
Popular accommodation
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC, Quarry Landing - Center of Town & River View - 3 Bedroom, Chesapeake City Pool Retreat – Waterfront Stay in the Woods, Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay , Eastern shore beachfront cottage with stunning sunset views!, Be persuaded to experience this vintage cottage by the Sassa, Walk to Town & River: Charming Home in North East!, Waterfront Cottage on the C&D Canal!, Charming 2-bedroom water oriented cottage with water access

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$155 per night from 23 Feb to 24 Feb
AU$155
23 Feb - 24 Feb
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$149 per night from 3 Mar to 4 Mar
AU$149
3 Mar - 4 Mar
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$169 per night from 22 Feb to 23 Feb
AU$169
22 Feb - 23 Feb
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
Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy Dover DE
Fully refundableReserve now, pay when you stay
The price is AU$124 per night from 16 Feb to 17 Feb
AU$124
16 Feb - 17 Feb
includes taxes & fees
With a stay at Bally's Dover Casino Resort in Dover, you'll be a 2-minute walk from Dover Downs Casino and 7 minutes by foot from Dover Mall.
Opens in a new windowBally's Dover Casino Resort
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.