Family-friendly vacation rentals in Cambridge

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Cambridge

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Annapolis

4.94 out of 5 average rating, 388 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end, brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens, lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 10.

Guest favorite

Apartment in Annapolis

4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Superhost

Home in Queenstown

4.81 out of 5 average rating, 156 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Guest favorite

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favorite

Home in Frederica

4.92 out of 5 average rating, 323 reviews

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

Top guest favorite

Place to stay in Annapolis

4.94 out of 5 average rating, 119 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Guest favorite

Apartment in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Superhost

Home in Annapolis

4.85 out of 5 average rating, 221 reviews

Spacious Home in Private Neighborhood with Beach

A beautiful and spacious home located on the Severn River in the gated community of Epping Forest! The house is just 7 miles from downtown Annapolis and offers guests a private, secluded home away from home. A private beach and club house are located within walking distance! Enjoy a fire on either of the two levels of private decks, or gather around the large dining room table for any of the provided board games. An abundance of amenities will make your stay more than comfortable!

Top guest favorite

Home in Fruitland

4.97 out of 5 average rating, 128 reviews

Amazingly convenient yet secluded.

Our place has views; the yard has beautiful shade trees that set the mood for deep relaxation. One can walk to Walmart, Denny's, Hampton Inn Suites, Ruby Tuesdays and many other business's in minutes. Ocean City is about a 35minute drive. Salisbury University is a five minute drive. UMES is a 13 minute drive.This home is ideally located. A retired teacher on one side is your closest neighbor; on the other property is a caregiver. Needless to say this is a very safe place; enjoy.

Guest favorite

Apartment in Deale

4.91 out of 5 average rating, 620 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Top guest favorite

Home in Lusby

4.99 out of 5 average rating, 294 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

Top guest favorite

Guest suite in Annapolis

4.95 out of 5 average rating, 192 reviews

Cozy Naptown Perch

Perfectly Placed Perch in Murray Hill neighborhood. 1 mile to USNA stadium; 1 mile to historic downtown. Walk to local restaurants, in town events. Few blocks to water access. 2 bedroom upstairs suite recently renovated. Common room has sofa, table and chairs, coffee/ tea set up. Patio, fire pit available to guests.

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What guests are saying

Osprey's roost: Spring and summer 2025

4.97 out of 5 average rating, 159 reviews6 days ago

We had such a wonderful stay at this home! I visited with my three young kids and there was never a dull moment—so many fun activities to do, both indoors and out. We loved having access to the kayak and canoe, which we used on both the ocean and the nearby lake. The location was peaceful and quiet, perfect for relaxing, and we had a blast fishing right off the dock. Inside, the house was cozy, spotless, and very comfortable. The beds were clean and comfy, and the kitchen was fully stocked with everything we needed—including spices and condiments, which made cooking easy. There were also tons of games to keep the kids entertained during downtime. The hosts were incredibly friendly, responsive, and proactively helpful, checking in by text and making sure we had everything we needed. I highly recommend this place and would absolutely come back!

Home in Hague

What guests are saying

Modern Apartment over the Heart of Main Street!

4.82 out of 5 average rating, 762 reviews4 days ago

You couldn’t ask for a better location in downtown Annapolis. Everything was outside of your doorstep with restaurants and shops just around the corner. It is a beautiful downtown and waterfront. This was my first Airbnb experience and I couldn’t be more pleased. It was located above a restaurant with easy access and parking. The two bedroom complex was very modern and the owner was very accommodating. Understand that you are in the beautiful and busy downtown area and as long as you don’t mind a little bit of the downtown experience below you, it will be a great place to stay. I would definitely recommend this location for anyone who wants to experience everything downtown within walking distance. I will definitely go back to this location again, if it becomes available in the near future.

Apartment in Annapolis

What guests are saying

Cottage #6 Wild Goose on the left of Main House

4.82 out of 5 average rating, 38 reviews20 months ago

If you are looking for a place to disrupt busy life & a place to chill with a waterfront view, Harris Cove Cottages Bed 'N Boat is just what you are looking for! (Harris Creek is a tidal creek tributary in Chesapeake Bay.) We had a cozy & relaxing stay in a waterfront cottage. The accommodation got the basic needs taken care of. Catching Blue Claw Crabs was plentiful from both going out on a boat & from their docks. We brought our own crab traps & made use of their ice machine for keeping our live catches fresh then used their steam station to prepare our crabs. They provide use of their kayaks, canoes, & even have life vests (bring your own for young kids) free of charge. They offer power boat rentals, or you can bring your own & use their dock. Our young child absolutely enjoyed exploring & already talks about returning. Family fun time! Would we revisit? Absolutely & looking forward to it! 💗 Alexander & Jamie are excellent & friendly hosts offering a serene oasis! ⭐⭐⭐⭐⭐

Cottage in Saint Michaels

What guests are saying

"Wittman Cottage"

4.89 out of 5 average rating, 159 reviews3 weeks ago

This was my 2nd visit to Lace’s home and would return again! I greatly enjoyed the private, quiet and peaceful surroundings, with views of Harris Creek from both the front and rear of the home, yet just a short drive to the shops & restaurants of St. Michaels and only 30 minutes to Easton. My favorite part? The huge screened in porch with lots of comfy furniture facing the water. With a dock, fire pit, outdoor eating spaces & included kayaks you, relatives & friends will enjoy yourselves at this spacious home.

Cottage in Wittman

What guests are saying

Perfect Eastport location

4.98 out of 5 average rating, 123 reviews3 weeks ago

Our family had a perfect stay in Eastport. This spot is tucked away in a quiet neighborhood within a block of one of a maritime museum and a beautiful and accessible dock, and a great restaurant/bar around the corner. Annapolis is a short walk away. This location is perfect.

Apartment in Annapolis