House holiday rentals in Saint Michaels

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Popular amenities for house rentals in Saint Michaels

House rentals with a pool

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

House in Edgewater Maryland

NancyRating, 5 stars3 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 favourite
Home in Rock Hall
4.95 out of 5 average rating, 37 reviews

Rockfish Keeper

Mary JaneRating, 5 stars1 week ago
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"
Guest favourite
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!
Guest favourite
Home in Severn
4.88 out of 5 average rating, 164 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

LoisRating, 5 stars1 week ago
Staying here made our family wedding stay away from home, a very memorable and fun weekend for the whole family. Muvh better than being stuck in a hotel with lots of kids!!
Guest favourite
Home in Montross
4.99 out of 5 average rating, 151 reviews

Beach Please! River cottage w/private beach & dock

AudreyRating, 5 stars1 month 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.
Guest favourite
Home in Fort Washington
4.91 out of 5 average rating, 150 reviews

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

CurtRating, 5 stars2 days ago
Simple, clean and well organized place .. would definitely recommend.
Top guest favourite
Home in Tracys Landing
4.99 out of 5 average rating, 207 reviews

The Little Gypsy BoHome

LaurenRating, 5 stars1 week ago
I can’t say enough wonderful things about Melissa’s place. As soon as you walk in, you feel right at home. She has thought of every possible thing you could need while there. The views were absolutely magnificent and while the beach area is available to the public, it felt super private. My daughters and I plan to come here every year. I had to peel them away from the bay. Melissa, thank you for accommodating us. This was a weekend my girls and I desperate needed and your home was the perfect place to have peace and intentional quality time. Thank you so much!!

Weekly house rentals

Guest favourite
Home in Capitol Hill
4.95 out of 5 average rating, 188 reviews

Beautiful Capitol Hill Row House

Mary FranRating, 5 stars2 weeks 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.
Top guest favourite
Home in Salisbury
4.98 out of 5 average rating, 196 reviews

Beautiful Renovated Home, Perfect Getaway!

DanielleRating, 5 stars3 weeks ago
This was our second time staying at this rental and we would recommend to others. Ann's communication was great and she even gave us the option to check in early and check out late as it was available.
Top guest favourite
Home in Salisbury
4.87 out of 5 average rating, 123 reviews

Hudson House

WendyRating, 5 stars5 months ago
We had an amazing stay at The Hudson House. Immediately after walking in, I felt right at home. The house was big, but so cozy. This was my first Airbnb but definitely won’t be my last. Allen was always very quick to respond to my messages. He also had a very friendly tone to his messages. I have family in Salisbury. This will be my go to place, if available, each time I visit Salisbury.
Guest favourite
Home in Greenwood
4.8 out of 5 average rating, 123 reviews

Country Retreat - 2BR apartment; day trip to beach

JuanRating, 5 stars1 month ago
Patrick was a great host and responded quickly to different inquiries prior and during my stay. The home was beautiful and was perfect for a fun and relaxing weekend away which was exactly what I was looking for. Would come back again
Superhost
Home in College Park
4.83 out of 5 average rating, 179 reviews

Spacious relaxing home by DC, CP, woods & lake

KarenRating, 5 stars3 weeks ago
Such a lovely, comfortable home. Everything we needed. Loved the location. The neighborhood was extremely quiet and neighbors were friendly. There's a park with walking trails and lake half a mile walk away. The house was perfect. Relaxing. Comfortable beds and bedding. The record player was an added bonus, as were the puzzles and board games for the rainy days. Communication was excellent. Answered any questions quickly and was very helpful. Would definitely stay here again.
Guest favourite
Home in Deale
4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

CarolRating, 5 stars2 weeks ago
Our family had a great time - the property was spacious and clean, location was beautiful, and we loved playing outdoors in the open space and getting out on the water. Hosts were very responsive and everything we might need/want was provided!
Superhost
Home in Salisbury
4.84 out of 5 average rating, 32 reviews

Comfy Belle House "Relax in the HotTub"

MicheleRating, 5 stars6 months ago
Quaint house in a beautiful established neighborhood. Lovely front porch and back deck to enjoy time outside. hot tub was great. Nice walk to lake and playground. Here for a baseball tournament and the house was perfect to come home to. Everything we needed, especially comfortable beds and cozy spaces to chill.
Guest favourite
Home in Suitland
4.88 out of 5 average rating, 16 reviews

Spacious 7BR/5BA Retreat: 15 mins to National Mall

KimberlyRating, 5 stars1 month ago
⭐️⭐️⭐️⭐️⭐️ Absolutely Perfect Stay! Our stay at Suitlamd Manor, was nothing short of amazing! From the moment we arrived, everything was spotless, well-organized, and exactly as described. The attention to detail—from the cozy decor to the thoughtful amenities—made us feel right at home. The location was perfect, close to everything we needed. yet still peaceful and quiet for a restful stay. Meka was an exceptional host, always responsive and helpful with local recommendations. We truly appreciated the little extras, like complimentary coffee and wine. The bed was incredibly comfortable, and we had everything we needed for a relaxing getaway. I highly recommend this place to anyone

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 stars3 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.
Guest favourite
Home in Wyoming
4.96 out of 5 average rating, 25 reviews

Charming Home in Camden Wyoming

TaraRating, 5 stars3 months ago
Vinay’s Airbnb was cozy, clean, and perfect for our stay. He was incredibly accommodating, especially for a late arrival and during a major snowstorm—walkways were shoveled and salted, which made everything so much easier when we arrived. We also appreciated the thoughtful touches like bottled water and new toothbrush kits, which were a lifesaver when my son left his toothbrush at a hotel in another state. Highly recommend and would definitely stay here again!
Top guest favourite
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!
Top guest favourite
Home in Shady Side
5 out of 5 average rating, 164 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

DeanneRating, 5 stars1 week 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!!
Top guest favourite
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!
Superhost
Home in Centreville
4.63 out of 5 average rating, 92 reviews

Peaceful Acres Guest House (A Nature's Getaway)

AnneRating, 5 stars6 months ago
The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.
Superhost
Home in Pentagon City
4.93 out of 5 average rating, 170 reviews

LA Inspired Glasshouse 4min DC| Hot Tub +Ping Pong

MorganRating, 5 stars3 weeks ago
We had a wonderful time staying at this beautiful home. We were pleasantly surprised at the cleanliness of this home when coming in. The beds were extremely comfortable in all of the bedrooms. Great communication and very kind host! Thank you Franck!
Guest favourite
Home in Pasadena
5 out of 5 average rating, 52 reviews

Waterfront CHeerful 2 with Private home

DavidRating, 5 stars3 weeks ago
The cottage /house was peaceful on the edge of an inlet from the Bay. The patio was lovely. It was chilly so we couldn’t use the kayaks. The kitchen was very well equipped. The dishes, utensils, cookware were quality. The extra cozy blankets were nice. He responded to a request very timely. We enjoyed the stay very much.

Quick stats about house rentals in Saint Michaels

  • Total rentals

    20 properties

  • Nightly prices starting at

    £135 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    20 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. Talbot County
  5. Saint Michaels
  6. House rentals