Guesthouse holiday rentals in Chesapeake and Ohio Canal

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Popular amenities for Chesapeake and Ohio Canal guesthouses

Family-Friendly guesthouses

Guest favourite
Guesthouse in Purcellville
4.81 out of 5 average rating, 275 reviews

Barn Apartment in VA Wine Country

CodyRating, 5 stars2 months ago
An extremely welcoming place that had many things to do and accommodating our autistic children very well! It was a shame we didn't get the chance to make s'mores! We would love to come back to this place sometime since it is so peaceful and homey! We watched older movies that we forgot about! Thanks for the DVDs!
Top Guest favourite
Guesthouse in Aspers
4.92 out of 5 average rating, 396 reviews

Cottage on our horse farm

FrancisRating, 5 stars1 week ago
I can't wait to go back! The house itself was more than comfortable for 2 very large dogs and my husband and I. The property is very serene, private and just beautiful! Sitting outside you can watch their 3 horses in the pasture or look at the lake (or walk around it) with it's gorgeous white water lilies. If your looking for a place to destress or just looking for a quiet area, this is the place. My dog's go 160 and 114, so you can bring your pups here too
Guest favourite
Guesthouse in Galesville
4.95 out of 5 average rating, 171 reviews

Nautical Charm and relaxing waterview!

StanleyRating, 5 stars4 days ago
Felt like a home-away-from-home! So much more than a hotel room. Very peaceful area with a very good view. Bed was comfortable. It was obvious that Pam cares about her clients I will be recommending this to others.
Top Guest favourite
Guesthouse in Boston
4.98 out of 5 average rating, 194 reviews

The Bunkhouse- simple & serene w/mountain views

EmmaRating, 5 stars3 weeks ago
What a treasure! My mom and I got away for a couple days at Jenn’s place (a wellness sanctuary) and it was so peaceful and lovely, despite the rain we ran into! The place is tranquil both inside and out (a backyard meadow you can frolic in!), and the amenities are wonderful. Fresh bread, eggs, cream (dairy and non-dairy!), butter were all delicious, and I was so obsessed with the local teas and other goodies that I had to go visit the local apothecary that sold them. Jenn and her partner were super responsive to every need, bringing us eye masks and extra cream! Bonus - book a massage with Jenn. Seriously one of the best I’ve ever had. We had a wonderful time, thank you! Hope to be back!
Guest favourite
Guesthouse in Frederick
4.97 out of 5 average rating, 339 reviews

The Shady Bear Cabin

CassidyRating, 5 stars1 week ago
This is a beautiful, private place with amazing nature. We saw deer and hummingbirds, and they were pretty close to us. This place has a wonderful cat (Mr. Moo) who will give you much love! It is a bummer that we didn’t see dogs, but we got to see the chickens and got eggs from them! Amazing place! Although we may not hear beautiful sounds like others mentioned, we felt the peace and mindless presence. We enjoyed our time, and it was a perfect place for our short retreat.
Top Guest favourite
Guesthouse in Manassas
4.93 out of 5 average rating, 100 reviews

Private Luxury Retreat Close to everything!

OscarRating, 5 stars1 week ago
We had a great stay! Check in instructions were clear and the space was clean and well-kept. Check out was a breeze as well. Monica was always responsive and friendly.
Top Guest favourite
Guesthouse in Gettysburg
4.99 out of 5 average rating, 434 reviews

The Cock and Feather Guesthouse

DonaldRating, 5 stars2 days ago
The decor and furniture enhanced the Gettysburg experience. The location was adjacent to the battlefields. Private and cozy .
Top Guest favourite
Guesthouse in Highland
4.98 out of 5 average rating, 290 reviews

Woodland Retreat

BrianRating, 5 stars1 week ago
Martha's place is a lovely retreat. There is enough privacy between the main house and the guest house. The guest house is spacious and comfortable with a great screened in porch and access to the pool. It's in a quiet and peaceful area. I look forward to coming back again.

Guesthouses with a patio

Guest favourite
Guesthouse in Mount Airy
4.96 out of 5 average rating, 125 reviews

Treasured Hideaway on the Hill

DianeRating, 5 stars3 weeks ago
The bed is probably the most important thing for us when choosing a rental. The master bedroom bed was excellent. The second bedroom, not so much. But if you don’t have back issues, it’s ok. We are really bed snobs 🥺
Top Guest favourite
Guesthouse in Washington
4.95 out of 5 average rating, 213 reviews

GardenLevel 4BR/2.5BA-Parking+By Convention Center

MariellaRating, 5 stars2 weeks ago
Alma’s place was fully renovated, beautiful finishes, gorgeous floors, super comfortable beds and impecable bathrooms. Kitchen was modern and had everything needed for cooking. Excellent location and walking distance grocery store. Alma was friendly and promptly answer all of our questions. She also allowed us to leave our luggage before check in time. We had a wonderful time and will be back for sure!
Top Guest favourite
Guesthouse in Lancaster
4.97 out of 5 average rating, 318 reviews

Cozy Cottage with back yard

MikeRating, 5 stars5 days ago
The cottage is exactly as described and pictured in the listing. It was clean and had everything needed for a short stay. Great place to stay if you are in the area for Spooky Nook as we were (about a 15 min drive). Kathryn and Martha were perfect hosts and great with communication. I highly recommend staying here.
Guest favourite
Guesthouse in Alexandria
4.92 out of 5 average rating, 145 reviews

The Guest Suite

KyleRating, 5 stars4 days ago
Very comfortable stay! Grateful for the dog friendly accommodations while in town for a wedding. The suite was well equipped and nice to have a kitchen for light meal prep. Convenient location with Uber for wedding events. Lindsey was very responsive and friendly. Would stay here again!
Guest favourite
Guesthouse in Washington
4.88 out of 5 average rating, 245 reviews

Adorable English Basement on 15th St

AlexRating, 5 stars1 week ago
Enjoyed a great stay here during World Pride! Very walkable to the Metro. Felt safe walking around late at night. Space was clean with a very comfortable bed. Would definitely recommend!
Top Guest favourite
Guesthouse in Orange
5 out of 5 average rating, 256 reviews

Taj Garage Guesthouse

AnnaRating, 5 stars3 weeks ago
The Taj Garage never disappoints! We first stayed here about three years ago and its standards have not dropped since. Highly recommend this darling accommodation.
Top Guest favourite
Guesthouse in Towson
4.98 out of 5 average rating, 166 reviews

Sunny Guesthouse steps from Towson!

BarbraaRating, 5 stars2 weeks ago
Megan's Sunny Guesthouse has become our home away from home when we go to Baltimore to visit our grand kids. It is a spacious room over a garage that was once an office. Has a small kitchenette, small desk, sofa, TV and table for eating and a nice shower. In addition, Megan is a very responsive host. Great find.
Top Guest favourite
Guesthouse in Edgewater
4.98 out of 5 average rating, 116 reviews

1 large room efficiency in detached garage.

ThomasRating, 5 stars1 week ago
5 stars for sure! The detached garage was even nicer than the photos! The neighborhood was so peaceful and had coffee just a short walk away. Rams Head on Stage was a blast of a concert venue too! Thanks Jocelyn for the awesome stay, pets, and local recommendations :) I would absolutely stay here again and strongly recommend

Guest house rentals with a washing machine and dryer

Guest favourite
Guesthouse in Washington
4.91 out of 5 average rating, 185 reviews

2 Level Guest House on Capitol Hill w/Parking

AbbyRating, 5 stars4 days ago
The home was comfortable, easily accessible and great for the price. host was incredibly friendly and responsive and was willing to help with anything. Will definitely rent this home again if we're in the area
Guest favourite
Guesthouse in Annapolis
4.9 out of 5 average rating, 290 reviews

Calico Cottage Guest House, king bed, free parking

KatherineRating, 5 stars6 days ago
Ann was extremely accommodating for me as I had to book the cottage so last minute. She get it all ready within a couple hours for me and made adjustments to her own schedule with a contractor for me to stay and make sure it was peaceful while I was working remotely. This is above and beyond what I needed and the consideration after she already helped get me in was just the cherry on top. The location is so perfect. Tucked away enough from downtown Annapolis for some peace and quiet, but close enough to enjoy every the town has to offer. The bed is big and comfy and it just feels like the perfect, quaint place to stay. I highly recommend staying at Ann’s cottage!
Top Guest favourite
Guesthouse in Columbia
4.97 out of 5 average rating, 209 reviews

The Carriage House-Serene, Rural Setting w/Firepit

ChristopherRating, 5 stars1 week ago
This place from top to bottom has everything you need. It’s peaceful, beautiful, modern and comfortable. I really love it here
Guest favourite
Guesthouse in Lusby
4.96 out of 5 average rating, 187 reviews

Cozy Lakeside Studio Retreat.

ChrisRating, 5 stars1 week ago
We celebrated our 19 year anniversary and my 48th Birthday at Logan’s place. The serenity of the lake and backyard was exactly what we needed to relax and recharge. We ate crabs by the lake, went kayaking multiple times, enjoyed sitting around the fire pit listening to music and having coffee on the doc in the morning. The neighborhood is so quiet and peaceful. We walked to the beach multiple times and enjoyed the beautiful scenery. We brought bikes and biked around the neighborhood too. Solomon’s island is very close and on the way to Logan’s we enjoyed the boat ride at the Maritime Marine museum and lunch at the Tiki bar, but we didn’t need to drive anywhere once we arrived since we had plenty of food and drinks. Everything was labeled clearly, which we appreciated. We loved the fresh flowers, chocolate mints as well as the shampoo, conditioner, coffee, cream, sugar, spices, qtips, cotton balls and even tooth brushes if you needed them. We would love to visit again.
Top Guest favourite
Guesthouse in Arlington
5 out of 5 average rating, 216 reviews

Private Sunny Cottage with King Bed + Yard / Patio

MarkRating, 5 stars3 days ago
Great stay…will definitely use again for extended stays in the area for business!
Top Guest favourite
Guesthouse in Earlysville
4.98 out of 5 average rating, 360 reviews

Cottage at Frog Jump- woodland privacy at its best

JenniferRating, 5 stars1 week ago
We just loved our stay at Frog Jump! Gail was the perfect host and even provided essentials when our baggage was delayed. Home made muffins awaited us in the morning and the bed was super comfy. Frog Jump was situated in a beautiful forest with a huge pond and lovely peaceful surroundings. The only thing missing was not enough time. Short drive to Charlottesville. Highly recommended.
Top Guest favourite
Guesthouse in Purcellville
4.98 out of 5 average rating, 241 reviews

The Cottage at Dunthorpe Farm

DeniseRating, 5 stars4 days ago
The farm cottage is a wonderful respite - clean, comfortable, peaceful. Kelly’s homemade breakfast pastries were delicious and the fruit was very refreshing. We were visiting family for our grandson’s high school graduation, so we regrettably were not able to explore the farm. We hope to return in the future to learn about the farm’s history and visit the horses. We loved having the dogs greet us when we arrived. If you are looking for a comfortable, quiet place to relax, this is the place. We have already recommended the farm cottage to another couple. Thank you Phil and Kelly
Top Guest favourite
Guesthouse in Annapolis
4.99 out of 5 average rating, 136 reviews

Garden View, a spacious 1 bedroom with loft.

MarieRating, 5 stars3 weeks ago
Sally’s place was a perfect ‘getaway’ to get some work and dissertation writing in. She was super nice to bring me an office chair, and her husband provided freshly baked cookies! My dog, Bagel, loved watching the wildlife out the window. The neighborhood is cute and peaceful but also close to anything you want to do or eat. The thoughtful touches and top-notch stock of kitchen items made my stay so enjoyable. I didn’t get to enjoy the backyard amenities but will be back for that and to explore more. Wonderful place and hosts, plus an adorable furry host!

Destinations to explore