House vacation rentals in Chesapeake Ranch Estates-Drum Point

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Popular amenities for Chesapeake Ranch Estates-Drum Point house rentals

House rentals with a pool

Guest favorite
Home in Edgewater
4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars2 weeks ago
Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.
Superhost
Home in Queenstown
4.81 out of 5 average rating, 156 reviews

Bay Breeze Retreat

EeshaniRating, 5 stars8 months ago
Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.
Guest favorite
Home in Cambridge
4.96 out of 5 average rating, 112 reviews

Gorgeous, waterfront home - Perfect for Families.

Leslie RogersRating, 5 stars5 months ago
We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!
Top guest favorite
Home in Edgewater
4.98 out of 5 average rating, 53 reviews

Entire Beach House with Pool and Hot Tub

DianeRating, 5 stars5 months ago
We had a great stay at this clean, comfortable, convenient and cozy house. We were impressed by the attention to detail. Every time we needed something, it was there. The kitchen was fully stocked and had everything we needed to cook our Thanksgiving meal. We were close to Annapolis And had an easy drive to the museums of DC. We took several walks to the nearby beach, and enjoyed both sunrises and sunsets. We would definitely come back! Thank you, Peggy!
Guest favorite
Home in Montross
4.99 out of 5 average rating, 151 reviews

Beach Please! River cottage w/private beach & dock

AudreyRating, 5 stars3 weeks ago
This was our second stay at Beach Please and it was just as delightful as the first! The house was again squeaky clean, thoughtfully decorated and had plenty of room for our multi-generational family to spread out. Grandparents appreciated the first floor master bedroom and kiddos loved the game room, and the crafts and puzzles upstairs. The neighborhood is peaceful and cozy, with beautiful views in every direction. The addition of the acoustic guitar for songs by the firepit was a major plus, as our ten year old is a music lover and almost brought her own. We had a great stay and would recommend this AirBnB to anyone! Grab a week (or two) and don't think twice.
Superhost
Home in Port Republic
4.75 out of 5 average rating, 20 reviews

Family Friendly: Hot Tub, Grill, Pool & More!

JosueRating, 5 stars2 weeks ago
Me and some friends stayed here and we all loved it. More than enough space and so much stuff/activities from movie nights to playing pool to hitting the hot tub and more to do in the house! We would definitely stay here again and the host was great.
Guest favorite
Home in Fort Washington
4.91 out of 5 average rating, 149 reviews

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

AndreaRating, 5 stars1 week ago
It was simply amazing. Daniel was a fantastic host. The house was incredible. Spacious, beautiful and peaceful felt just like home. The family and I enjoyed every inch of it. Family vacation home for every trip we take to DC.
Superhost
Home in Annapolis
4.71 out of 5 average rating, 69 reviews

Bay Poolhouse

KimberlyRating, 5 stars4 months ago
We really enjoyed staying here. It was a spacious home and we love the community. We were in town visiting family and It was so convenient being so close to family and friends. Very comfortable

Weekly house rentals

Superhost
Home in Wye Mills
4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars11 months ago
Kevin is a great host to us year after year! we love staying at his place!
Guest favorite
Home in Capitol Hill
4.95 out of 5 average rating, 187 reviews

Beautiful Capitol Hill Row House

Mary FranRating, 5 stars1 week ago
Maggie’s house was perfect for our family getaway! You can’t beat this location. It was a quick walk to Eastern Market metro and tons of local shopping/dining options, yet the street was peaceful and quiet. We were able to spread out and relax as a family of three with two dogs. The house was comfortable and had everything we needed. Maggie was responsive and helpful from booking and through our stay. 10/10, would book again.
Guest favorite
Home in Northwest Washington
4.93 out of 5 average rating, 60 reviews

Light-Filled Victorian Town-Home

SusanRating, 5 stars3 weeks ago
Stuart's place was exactly as pictured. his home was clean and welcoming. Everything was walkable, with many bars and restaurants nearby. The beds were extremely comfortable, and we slept soundly each night. The neighborhood is terrific, and the Sunday farmers market is held practically next door. Stuart was very quick to respond to my questions both before and during our trip. We will definitely stay here again, the next time we are in town. If you are looking for a home away from home in DC, don't look any further than this fabulous house. You won't be sorry.
Guest favorite
Home in Arlington
4.83 out of 5 average rating, 12 reviews

Wonderful DC 2-miles away-Parking-Super Convenient

RhondaRating, 5 stars1 month ago
Robert's place is comfortable and clean. The mattresses are comfortable - firm with a soft top. He is friendly, responsive, and full of information about the area. We felt completely at home. It is the perfect distance from the mall. We took an Uber into the city each day and this was an easy, quick, and inexpensive ride.
Top guest favorite
Home in Shady Side
5 out of 5 average rating, 164 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

DeanneRating, 5 stars6 days ago
Absolutely amazing house and location!! Our family had an incredible week spent enjoying the property & views, spending time watching the sunsets by the fire, and kayaking around the bay. It's a great spot to teach kids to paddle and our 7 and 9-year old both enjoyed learning on the still waters near the sandy beach. The property and house are both thoughtfully designed and have so many spots to relax, read, watch the birds, and take in the views - made it feel like there was never a reason to leave. We had an incredibly peaceful week and would love to visit again!!
Superhost
Home in Upper Marlboro
4.83 out of 5 average rating, 6 reviews

Beautiful spacious 4-bedroom home w/2-story lounge

BryanRating, 5 stars2 weeks ago
Nice place, had an issue with the ac but they had issues resolved quickly.
Top guest favorite
Home in Cambridge
4.95 out of 5 average rating, 231 reviews

Great Historic Cambridge Home With Parking!

AshleyRating, 5 stars1 month ago
What a gem! My daughters and I loved our week spent here. The home is a true beauty with all the charm of a seaside getaway. All of the amenities truly made it feel like home, and the kitchen is amazing! Everything was streamlined and easy, the host was wonderfully responsive, and the home had such a friendly, warm, relaxing feel to it. It was such a terrific experience through and through, I would highly recommend taking full advantage of this beaut!
Guest favorite
Home in Port Republic
4.88 out of 5 average rating, 25 reviews

Magical Bayfrnt Home, Pier, Beach, Fossils, trails

SkyeRating, 5 stars3 months ago
An extraordinary place to rest & recharge. The views, the comfort of the home, and the gorgeous walking trails, through woods & beach are a perfect combination. Everything we needed & then some.

Private house rentals

Superhost
Home in Fort Washington
4.82 out of 5 average rating, 106 reviews

Home away from home near MGM-3bed2bath

FrankieRating, 5 stars2 weeks ago
The space was exactly as described! Very clean and host was very proactive with check in and out instructions. Had a great time visiting the area. Would absolutely stay here again! **to note: there is a resident who lives downstairs, which is noted in the Airbnb description. You can hear them when they enter/exit the home. This did not bother us at all and we were aware of this as it was in the description but I wanted to highlight that for any perspective guests.
Top guest favorite
Home in Arlington
4.97 out of 5 average rating, 100 reviews

Entire family size house steps to ANC & metro walk

Mary EllenRating, 5 stars1 month ago
Tyler's place was perfect for our stay with our extended family. It's spacious and comfortable, with plenty of room to relax indoors and out. It has a very nice large porch and deck, great for some solitude or for kids to play. The beds were comfy and the linens ample, there are gorgeous large bathrooms and luxurious showers, the kitchen was well-stocked and included an amazing high-end stove, and the living spaces are nicely decorated and furnished with art and tons of books. One bedroom had lots of toys and kids' books, a very nice touch. Tyler was helpful, accommodating, and responsive. The location is very convenient to Arlington National Cemetery and within walking distance to a Metro stop. Everything about this rental was fantastic--we highly recommend it if you need a lovely space for a large group. Thanks, Tyler!
Top guest favorite
Home in Taylors Island
4.97 out of 5 average rating, 39 reviews

A Vacation for All, Away From It All

ChristyneRating, 5 stars5 months ago
If you are looking for a peaceful escape, you found it. Although this home can be used for large gatherings, it is also the perfect getaway for 2. My husband and I loved watching the water and the natural wildlife. DO NOT MISS THE OPPORTUNITY TO EXPERIENCE THIS HOUSE!
Superhost
Home in Northeast Washington
4.88 out of 5 average rating, 51 reviews

VIP 2King Bed, DC Line, Free Parking, WIFI

BebeeRating, 5 stars1 week ago
Aivet’s place was very beautiful and spacious. We truly enjoyed our stay there as well. We highly recommend it to anyone who’s looking to travel and relax at the same time. Everything we needed was right there as well. Hopefully, we’ll get the opportunity to visit again soon. Thank you for being an amazing host.
Guest favorite
Home in Saint Michaels
4.94 out of 5 average rating, 49 reviews

Private&Cozy/3br+2ba/1mi to town

ScottRating, 5 stars2 weeks ago
I have never stayed in a place that absolutely had everything we needed. I could have brought my clothes, shoes and makeup and basically been fine. The house was very clean. The furniture was comfortable and clean. The beds were comfortable. Town was 5 minutes away. We loved the shops and great restaurants. We would definitely recommend this house.
Guest favorite
Home in Northwest Washington
4.98 out of 5 average rating, 116 reviews

Charming Bloomingdale Row Home with Deck & Parking

JasonRating, 5 stars5 days ago
My wife, two kids, pup and I all enjoyed our stay at this well appointed and super comfy home. It is in a great location with parking on site and a cute park right out the back door. Walk to lots of cute restaurants, bus and metro easily. The host was super accommodating and easy to get in touch with. Will definitely stay here again if ever in the DC area.
Superhost
Home in Northwest Washington
5 out of 5 average rating, 5 reviews

4 bed townhouse + in-law suite

AnandRating, 5 stars21 months ago
my family and I had an amazing time at Julia's place. She is an amazing host and the house was well furnished and we really enjoyed our 11 day stay there. look forward to coming back again.
Top guest favorite
Home in National Harbor
4.97 out of 5 average rating, 39 reviews

7BD Amazonia Duplex-style home

KirstenRating, 5 stars3 weeks ago
This home was perfect for 6 of us to stay. The beds were comfortable, the heat & AC worked perfectly for the fluctuating temps, the kitchen was well stocked, and there was great space both upstairs and down. I’d definitely stay here again!

Destinations to explore