House holiday rentals in Deale

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Popular amenities for house rentals in Deale

House rentals with a pool

Guest favourite
Home in Montross
4.98 out of 5 average rating, 107 reviews

Waterfront | Kayaks+Beach+Pool | Gameroom+Firepit

BrittanyRating, 5 stars2 weeks ago
Connie’s place was great! Looked just like the photos. The house was clean and in a great area. Nice and friendly neighbors. We enjoyed the community beaches that are super close, clean and dog friendly. It was a prefect weekend trip. We would book here again!
Superhost
Home in Montross
4.92 out of 5 average rating, 208 reviews

The Glebe

KristinaRating, 5 stars3 weeks ago
We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 116 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars3 weeks ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Guest favourite
Home in Severn
4.88 out of 5 average rating, 171 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

TiffanyRating, 5 stars2 weeks ago
Great home,had Everything you need to have a good time. The collection of books will make you go back to continue reading. Will recommend to all my ohio friends traveling to Maryland
Guest favourite
Home in Montross
4.99 out of 5 average rating, 156 reviews

Beach Please! River cottage w/private beach & dock

LisaRating, 5 stars2 weeks ago
Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.
Guest favourite
Home in Perry Hall
4.99 out of 5 average rating, 100 reviews

Gunpowder Retreat

MaryRating, 5 stars2 weeks ago
This home was spotlessly clean and looks just like the photos. The beds were comfortable and there was plenty of room and seating for watching movies. The showers and bathrooms were great, and it was nice to be able to do laundry. We used the pool towels provided. The kitchen was stocked with basic items - there is a keurig coffee pot only and they provide pods which was nice. A few things we didn’t realize: the driveway is very steep and we scraped our van trying to go down the first time - you need to go in at a certain angle. The noise alarms are very sensitive and it went off when we were watching a family movie, and we had to answer a text from Tanya. This was honestly a bit annoying. We enjoyed the pool and hot tub! When the jets were turned on, the hot tub become filled with much foam from all the chlorine so we didn’t turn the jets on anymore. We hiked from the house into the state park and did a 5 mile loop, which was very convenient.
Guest favourite
Home in Fort Washington
4.92 out of 5 average rating, 156 reviews

5 BEDR, Inground Pool+Billiard Table, Close To D.C

TheresaRating, 5 stars1 week ago
Daniel’s Home was beautiful and he made this special event for me and my family able to celebrate my sons 26th Heavenly Birthday a success We were very comfortable and it really felt like home the pool was very clean and the Home was very spacious and squeaky clean I would love to Book Daniel again He was a very nice and friendly Host that responded to any questions we had he made communication easy me and my family really enjoyed our self and yes he’s reasonable and you definitely get what you paid for and more Thank you again Daniel
Top guest favourite
Home in New Market
4.94 out of 5 average rating, 142 reviews

Historic Peace and Plenty Farm: Pool House

JenniferRating, 5 stars2 weeks ago
Duane and Matt were absolutely wonderful hosts! They helped make our quick weekend getaway truly unforgettable. Every amenity at the property was thoughtfully provided, and our daughters enjoyed every bit of it. Even while traveling internationally, Duane remained incredibly attentive and responsive, going above and beyond to ensure our stay was perfect. One of the highlights for our girls was getting to meet a baby sheep—such a thoughtful and special touch! They were especially taken with little Pinky Pie and are still talking about her. Thank you again, Duane, for sharing your beautiful property and creating such a memorable experience for our family!

Weekly house rentals

Guest favourite
Home in Chesapeake Beach
4.95 out of 5 average rating, 21 reviews

Mid-Century Modern: Direct Private Beach Access

LauraRating, 5 stars2 weeks ago
We returned to this gorgeous home for a second time this summer for a full week’s stay. Not only is the home, landscaping and views beautiful, the house is well equipped with everything we needed for a very comfortable stay, especially the kitchen. We enjoyed finding shark teeth on the private beach, relaxing in the hammock and taking drives into town which is just a short trip away. Nicholas was a super helpful and responsive host. Thank you for your hospitality and sharing your beautiful home! We’ll be back next year!
Top guest favourite
Home in Tracys Landing
4.78 out of 5 average rating, 41 reviews

Maple Treehouse in Maryland

EdRating, 5 stars1 month ago
Tara and Theresa were great! The place was just what was needed in every way! The host always made sure that the house was up to our needs and anything was immediately addressed. A top tier host without a doubt! Don't hesitate to book :)
Guest favourite
Home in Crownsville
4.93 out of 5 average rating, 15 reviews

Welcome to Heron House! Annapolis Waterfront Oasis

HaleyRating, 5 stars1 week ago
We had the best time enjoying Jody and Gail's beautiful home! The views were incredible, it was so peaceful, and the house had every amenity we could have wanted. A highlight was kayaking and swimming in the cove right to the side of the home. We cant wait to come back!
Top guest favourite
Home in Stevensville
5 out of 5 average rating, 37 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

ShadRating, 5 stars1 month ago
We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.
Top guest favourite
Home in Shady Side
4.98 out of 5 average rating, 58 reviews

"Pier Joy!" - 3BR Waterfront Home W/Private Dock

AmandaRating, 5 stars1 month ago
I have stayed at dozens of Airbnb’s and this is in my top 3! The home is perfectly appointed, super clean, well stocked, cozy, and beautifully decorated! The master bathroom is magazine worthy. Jeff was very easy to communicate with and let us check in early. My family plans to make it an annual trip.
Top guest favourite
Home in North Beach
5 out of 5 average rating, 23 reviews

Cozy Cottage By The Beach-Pet Friendly

HannahRating, 5 stars1 week ago
Adorable house with so many thoughtful touches, including a stocked kitchen. Five min drive or 15 min walk to the beach, with a beach pass included!
Superhost
Home in Shady Side
4.88 out of 5 average rating, 40 reviews

Baydream Believer -Chesapeake Bay water community

ChrisRating, 5 stars1 month ago
We really enjoyed our stay at this pet-friendly, charming house. The location was perfect—peaceful, scenic, and just a short walk away from the water. The house was clean, comfortable, and had everything we needed. The hosts were very responsive, accommodating, and easy to communicate with, making the whole process smooth from start to finish. We'd definitely consider staying here again and recommend it to anyone looking for a serene getaway in a quaint bayside community. Thanks Mary and Chris for a great stay!
Guest favourite
Home in North Beach
4.78 out of 5 average rating, 23 reviews

Safe Harbor at Herring Bay

MorganRating, 5 stars3 days ago
Chris’ home was spotless! It was also a quick walk to the nearby Herrington Harbour where we had wedding festivities all weekend. Chris was very responsive and offered cash back upon hearing the grill was unusable. Highly recommend!

Private house rentals

Top guest favourite
Home in Huntingtown
4.96 out of 5 average rating, 53 reviews

House near Patuxent River

JasonRating, 5 stars1 month ago
Erik is an excellent host. The pictures don’t do this place justice. Highly recommended and we will stay again.
Guest favourite
Home in Prince Frederick
4.9 out of 5 average rating, 10 reviews

Chesapeake Escape

LuzRating, 5 stars5 days ago
We had a great stay! The place was really clean and had great views of the beach.
Top guest favourite
Home in Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars2 weeks ago
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)
Guest favourite
Home in Shady Side
5 out of 5 average rating, 28 reviews

Peaceful Waterfront Getaway

MichelleRating, 5 stars1 month ago
Lovely stay at Tanya's house. Beautiful back porch overlooking a marina and working boatyard. The fire pit in the backyard was so perfect to gather around. Beds were very comfortable. Kitchen was spacious enough to allow our family to cook together and double oven an extra plus. We enjoyed an early morning kayak ride too with the kayaks Tanya provided! Tanya was a great host and super responsive to our questions. small note for sail boat owners, the water around her dock isn't deep enough to dock a sailboat. We would HIGHLY recommend this place as a great place to gather for family and friends!
Guest favourite
Home in Chester
5 out of 5 average rating, 9 reviews

Kent Island Escape

Maggie Rating, 5 stars1 week ago
We stayed at this beautiful airbnb during the transition of our house selling locally. It was a beautiful place to stay during our transition. Definitely come be a place to stay at again.
Top guest favourite
Home in Prince Frederick
5 out of 5 average rating, 16 reviews

Downs By The River

JeffRating, 5 stars2 weeks ago
We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!
Top guest favourite
Home in Pasadena
5 out of 5 average rating, 17 reviews

Rock Creek Cottage, Waterfront

JaneRating, 5 stars3 days ago
We loved this place! Perfect location for our festivities in Pasadena and very peaceful.
Top guest favourite
Home in Annapolis
5 out of 5 average rating, 42 reviews

Bay Home in Annapolis with Private Dock

ToddRating, 5 stars3 weeks ago
Beautiful place, beautiful location. Joel thought of anything you could want.

Quick stats about house rentals in Deale

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹7,740 before taxes and fees

  • Total number of reviews

    890 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Anne Arundel County
  5. Deale
  6. House rentals