
Family-friendly holiday rentals in Algonquin
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Top-rated family-friendly rentals in Algonquin
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Popular amenities for Algonquin family-friendly rentals
Family-friendly home rentals with a hot tub

Steps from Ironman MD Start
Fantastic house in a great location. The surrounding park is beautiful and the location is incredibly peaceful. The house was great and met our needs perfectly. Two beds and a pull out sofa. Living room and kitchen has everything you’d need. Check in and out was as simple as possible. Enjoyed staying here!

Nautical Vibe Walk 2 Harbor Pubs USNA
Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

Charming Annapolis Water View Home
This house is uncommonly beautiful. There is something in every space worthy of contemplation whether it is coffee table in the living room that has a turn of the century industrial feel to the lacquered kitchen countertop that has sealed in the natural beauty. I spent the weekend in awe of its intricacies. I was in town for a wedding with my family, but noted how the whole house including the outdoor space included everything a beachfront house would have to enjoy an extended summer vacation for the whole family. Outdoor space was well equipped for outdoor activities and entertainment with fire pits, grills, hot tub, a plugin cooler for outdoor use. I only wish we’d been better suited to enjoy every aspect of the amenities provided. My favorite thing about this place was the view of the Chesapeake in all of her glory on full display from the living room window. Delightful.

Annapolis Elegant 5* House -3 Bedrooms Sleeps 6
Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.

Celebrate Summer by Your Private Pool
Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa
This was a beautiful waterfront home! This home was well equipped with everything you may need! The host was available if we needed anything! Would definitely recommend!

Cozy waterfront getaway on the Bay
This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.

You'll Never Want to Leave
We thoroughly enjoyed our stay at Laurie's home! It was a great location and the home matched the description. We had everything we could have asked for and more, and Laurie was a great host. Would definitely stay there again!
Family- and pet-friendly home rentals

Premier St Michaels Cottage- In Town Location
Stayed here Memorial Day Weekend with my family of 4 and dog and had the most lovely time! The house is very clean and conveniently located to everything! Thomas was an excellent and communicative host. We will most certainly stay here again!

Perfect St. Michaels Getaway
This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.

Brand New Reno in Historic Dist w 2 Parking spots
We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.

Rockhold Creek Cottage
We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.

Historic St. Mary's City, MD
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

Hudson House
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.

Old World Cottage/Fabulous Sunsets/Polite Pets OK
Our stay in Tall Timbers was fabulous, much of it thanks to the care, detailed information, and lovely accommodations provided by our host, Robert. He communicated extremely well through the whole process from booking to check out. Nothing was a mystery and everything was as described or better. The house is charming and in a lovely wooded location. it's isolated but close to many amenities and short drive to historical attractions, local businesses, and the beautiful Maryland coast. We had a particularly wonderful visit to the Tall Timbers Oyster Ranch which is walking distance from the house. We highly recommend this location and send our thanks once again to Robert for his outstanding hospitality!

Perfect Bay and Beach Getaway one hour from DC!
Our stay was great. The house is located in a quiet friendly neighborhood. The views are amazing. The house is very comfortable and so relaxing. Loved that three bedrooms each had a bathroom. The hosts were wonderful and very responsive.
Family-friendly home rentals with a pool

True St. Michaels 6 Acre Waterfront w/heated pool
Great place for a getaway! St. Michael’s is a wonderful town and so easy to get to from this lovely place! Was perfect location for our family ladies trip- plenty of space and just a quick trip down town to the shops and restaurants! - I think we’ll be back!

Oyster Cottage
This little Cottage was absolutely perfect. Our stay was quick but it was exactly what we needed. Overlooking the water, listening to the birds, and enjoying the absolute peace that is Chincoteague. This is a spot I'll definitely be visiting again!

Heron Harbor
All I can say is WOW! We were blown away at the beauty of the home AND the view! Relaxing and peaceful. The pool was to die for and Kathleen was one of the best hosts I’ve ever had in all our air bnb travel!!! Will definitely return AND will check out her other properties in the future. Thank you to Kathleen and her staff/team!!

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*
We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

Turtle's Nest - Hist. Cambridge
David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

Annapolis Entertainment Complex
Outstanding home with so much to offer! The description is exactly what is offered. The kitchen has everything you need to prepare any meal. All bedrooms are spacious and comfortable. As far as the entertainment factor - WOW! The outside is beautiful and the pool and hot tub were fun to use. There’s so much available in this house. You will not be disappointed. Dan, the owner, was very easy to get in touch with and to work with. If you’re looking for something, ask Dan, he probably has it!

Horseshoe Haven
This was our 3rd time in Chincoteague in the past 4 years and we plan on visiting again in the future. The beach is easily accessible but has never seemed too crowded. We love watching the wildlife (especially the horses). There is plenty to do for the whole family. We really enjoyed our stay at this house from beginning to end. Communication with Gary and Renee was seamless. We spent a lot of time hanging out on the screened-in porch. We had plenty of ping-pong matches. We had a lot of fun in the pool also.
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- Sandy Point State Park
- Maryland Renaissance Festival
- Killens Pond State Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- Quiet Waters Park
- Baywood Greens Golf Maintenance
- Heritage Shores
- Ragged Point Beach
- Plantation Lakes Golf and Country Club
- Breezy Point Beach & Campground
- Gerry Boyle Park
- Brownies Beach
- Idlewilde Restoration Project
- Rose Haven Memorial Park
- Chesapeake Beach Water Park
- Six Flags America
- Downs Park Dog Beach
- Matapeake Clubhouse and Beach
- Quiet Waters Dog Beach
- Oxford Beach
- Piney Point Beach
- Lane Beach
- North Beach Boardwalk/Beach
- Bayfront Beach