Vacation rentals with a pool in Cambridge

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cambridge

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Cambridge

4.98 out of 5 average rating, 108 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Dec 24 – 31

G$53,889 GYD per night

Guest favorite

Apartment in Stevensville

4.98 out of 5 average rating, 240 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Mar 15 – 22

G$39,836 GYD per night

Guest favorite

Home in Stevensville

5.0 out of 5 average rating, 101 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Mar 8 – 15

G$199,783 GYD per night

Guest favorite

Home in Montross

5.0 out of 5 average rating, 120 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Oct 1 – 8

G$83,623 GYD per night

Guest favorite

Home in Chesapeake Beach

4.91 out of 5 average rating, 111 reviews

Indoor pool/spa nestled in Southern Md. woods.

Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles).

Jul 6 – 13

G$165,436 GYD per night

Superhost

Tiny home in Lincoln

4.83 out of 5 average rating, 230 reviews

Tiny house w/ Pool on water near Beaches / turf

Custom built tiny house located on Cedar creek, directly off of route one with Hot tub access.. 10 minutes from Delaware Turf and 15 minutes from the beach area. Tiny home comfortably sleeps four people. Waterfront view from the tiny house. We live on the property and are happy to help with your entire stay! We are contractor and long term rental friendly :) we also welcome Families with children or pets :) WE ARE PET FRIENDLY READ RULES IN "THE SPACE SECTION" BEFORE BOOKING

Mar 22 – 29

G$40,412 GYD per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Oct 15 – 22

G$111,838 GYD per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 208 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Jan 6 – 13

G$56,900 GYD per night

Guest favorite

Guest suite in Arnold

4.97 out of 5 average rating, 128 reviews

Pet Friendly Captains Quarters, Near Annapolis, EV

Yes, the hot tub IS open! 24/7/365 :-) This space has been fully updated with all the conveniences and amenities to make your stay enjoyable! We offer: - a king bed so you get a stellar night's sleep, - a queen bed sleeper sofa for family travels, - high speed internet, - a furnished kitchen, - private en-suite bathroom, and - a coffee bar. We're close to everything - located four miles from my hometown Annapolis!

Sep 21 – 28

G$40,417 GYD per night

Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 166 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower.

Nov 29 – Dec 6

G$96,017 GYD per night

Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 106 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Jun 13 – 20

G$83,524 GYD per night

Guest favorite

Home in Lusby

5.0 out of 5 average rating, 111 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Summer is a 1-week minimum, Friday-Friday* Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300 foot private beach. The year-round property has a pier, in-ground pool (May-October) with amazing river views.

Jun 25 – Jul 2

G$184,563 GYD per night