Pet-friendly vacation rentals in Arnold

4.97 out of 5 average rating, 472 reviews

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

4.97 out of 5 average rating, 133 reviews

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

Home in Stevensville

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

4.98 out of 5 average rating, 162 reviews

Two blue Adirondack chairs are positioned on a leaf-covered area, facing a tranquil body of water. Surrounding trees provide a natural frame, with autumn foliage adding warm colors. In the background, a wooden dock and shelter are visible along the water's edge.

Cottage in Annapolis

Waterfront farm retreat for vacation & telework

Stay on 125-acre Hollywood Farm in a beautiful and quiet home surrounded by water and woods. Our airy, mid-century renovated cottage feels like a sanctuary, tucked away on a peninsula on one of the largest tracts of conservation land in Maryland. This cozy, light-filled space is small but spacious, allowing you to work peacefully from home with a full desk and excellent high-speed internet access. Plus, there's a dock, kayaks, and lots of outdoor space for children and pets to run around in.

4.99 out of 5 average rating, 142 reviews

A Bullfrog hot tub is situated under a wooden gazebo, with water glistening in sunlight. A plush robe is draped over the edge alongside a straw hat and a rolled towel. A grassy area and wooden privacy fence complete the serene outdoor setting.

Home in Cape St. Claire

Beach Access, Hot Tub, Pet Friendly, Fully Fenced

A serene escape awaits you at our cozy hot tub 4-bedroom retreat, minutes away from Historic Downtown Annapolis. As the sun sets, the deck comes alive under the soft glow of string lights beckoning you to unwind in our 8-person Bullfrog hot tub or outdoor firepit where your worries will melt away! Indulge in the culinary delights of fresh local seafood and world-renowned crabcakes just moments away. Truly indulge in our paradise getaway and experience everything Annapolis has to offer!

4.99 out of 5 average rating, 145 reviews

A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.

Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

5.0 out of 5 average rating, 217 reviews

Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

4.95 out of 5 average rating, 216 reviews

Guest suite in Arnold

Pet-Friendly King Suite + Kitchen | Near Annapolis

Settle in just minutes from Annapolis in a spacious, pet-friendly guest suite with a king bed, full kitchen, separate living area, and year-round hot tub access. Perfect for couples, families, pet owners, and longer stays, Captain's Quarters sleeps up to 4 with a king bed plus a queen-size LoveSac sofa bed. Located just 4 miles from historic Downtown Annapolis and the U.S. Naval Academy, with private keyless entry, fast Wi-Fi, designated parking, and all the comforts of home.

4.94 out of 5 average rating, 147 reviews

Guest suite in Annapolis

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Place to stay in Glen Burnie

A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

4.94 out of 5 average rating, 413 reviews

A tranquil bedroom features a spacious bed adorned with a patterned throw and neatly arranged pillows. A modern lamp and decorative mirror enhance the ambiance, while natural light enters through a unique shaped window. A soft towel is elegantly rolled on the bed.

4.93 out of 5 average rating, 206 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!

4.99 out of 5 average rating, 167 reviews

A spiral staircase leads to a lofted sleeping area in a well-lit living space. Warm wood tones are present in the furniture and flooring. A small kitchen area is visible, along with a dining table set for four. Lighting fixtures enhance the modern feel.

Guesthouse in Annapolis

Garden View, 1 Bedroom and a Loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

A serene outdoor patio area features manicured hedges and a stone path. A seating arrangement is visible, surrounded by greenery. A colorful flag and artwork hang on the fence, while flowering trees add a natural touch to the space, providing a cozy atmosphere.

4.96 out of 5 average rating, 268 reviews

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.

Popular amenities for Arnold pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 267 reviews

Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.

Home in Edgewater

Annapolis Area Waterside Retreat

A modern kitchen features a large marble island with seating for several guests. White cabinetry and a stainless steel stove create a clean aesthetic. Natural light filters in through multiple windows, illuminating the thoughtful decor, including a chandelier and a vase with fresh flowers on the island.

4.98 out of 5 average rating, 161 reviews

Gorgeous Historic Downtown Annapolis House

4.96 out of 5 average rating, 114 reviews

Home in Odenton

Train Tracks Getaway (Whole house)

4.98 out of 5 average rating, 287 reviews

The living room features a light-toned couch centered in the space, complemented by a decorative coffee table. A reclined green chair and a lamp beside it provide additional seating. The open kitchen is visible in the background, with light cabinetry and full size appliances.

Home in Shady Side

Canary Pointe-A popular getaway for 2!

4.94 out of 5 average rating, 126 reviews

A bright living room features a dark sofa adorned with decorative pillows, paired with a wooden coffee table on a patterned rug. A decorative wall with framed pictures adds character, while natural light enters through the large windows covered by light curtains.

Home in Edgewater

Relaxing Turkey Point Retreat-Steps to the marina!

4.95 out of 5 average rating, 314 reviews

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

4.95 out of 5 average rating, 199 reviews

A cozy living area features a gray sectional sofa with a yellow throw draped over it. Wood accents and a patterned area rug complement the warm hardwood floors. An adjacent dining space is visible, showcasing a rustic brick wall and a dining table with elegant lighting.

Home in Fells Point

Charming 4 bedroom home just steps to the water!

4.98 out of 5 average rating, 155 reviews

Home in Deale

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

Pet-friendly home rentals with a pool

Guesthouse in Stevensville

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

Waterfront-View of Bay from your Bed

4.99 out of 5 average rating, 371 reviews

4.98 out of 5 average rating, 204 reviews

A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.

Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

4.99 out of 5 average rating, 255 reviews

A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.

Home in Tracys Landing

The Little Gypsy BoHome

Apartment in Upper Marlboro

Kone Oasis- hot tub, pool, theater/game rm.

4.94 out of 5 average rating, 218 reviews

Guesthouse in Stevensville

The side view of a historic brick house is shown, featuring a gabled roof with multiple chimneys. The whitewashed brick exterior contrasts with the green trim around the windows and door. The well-maintained lawn surrounds the structure, complemented by mature trees in the background.

Circa 1700 Chesapeake Colonial Home

4.92 out of 5 average rating, 197 reviews

Townhouse in Logan Circle

The private backyard features a stock tank pool surrounded by wooden benches with cushions, styled with colorful flowers and greenery. String lights create a warm ambiance, illuminating the space for relaxation and outdoor gatherings.

Historic Row Home Near Conv Center w/ Tank Pool

4.95 out of 5 average rating, 136 reviews

4.87 out of 5 average rating, 121 reviews

A cozy sleeping area features a spacious bed with cotton bedding and decorative pillows. Natural light enters through a window, highlighting the minimalist design. An ottoman rests at the foot of the bed, with a bedside table and a storage unit visible in the space.

Tiny home in Glen Burnie

Secluded Tiny House With your own Private Pool

4.98 out of 5 average rating, 313 reviews

A wooden table is set with a bottle of Walnut Crest Cabernet Sauvignon and two etched wine glasses. A red apple rests in a dark, leather-like bowl, with a serene backdrop of green foliage visible through a screened window.

Guesthouse in Highland

Woodland Retreat

Private, pet-friendly home rentals

4.87 out of 5 average rating, 118 reviews

A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.

Cottage in Annapolis

Charming City Retreat. Walk-harbor, eateries.USNA

4.92 out of 5 average rating, 189 reviews

Cabin in Gambrills

Relaxing Cabin Get Away Near Annapolis & DC

4.98 out of 5 average rating, 43 reviews

An aerial view showcases the stunning Heron House nestled on a waterfront point, surrounded by lush greenery and water. A spacious deck with outdoor seating and dining is visible, along with nearby boats docked along the shoreline under a twilight sky.

Home in Crownsville

Welcome to Heron House! Annapolis Waterfront Oasis

4.93 out of 5 average rating, 14 reviews

Home in Arnold

Fun-Filled Liberty Call w Porch, Parking, Gaming

4.96 out of 5 average rating, 23 reviews

Home in Cape St. Claire

Family Escape | Beach + Water + Shops Nearby

A spacious living area features a large sectional sofa with yellow accent pillows and a wooden coffee table. Natural light streams through three windows, illuminating a mounted flat-screen TV and surrounding shelves that hold decorative items. A cozy atmosphere is created by warm wooden flooring.

4.92 out of 5 average rating, 25 reviews

Pet-Friendly Annapolis Getaway | USNA & Beach/Bay

4.67 out of 5 average rating, 6 reviews

Home in Arnold

Coastal Modern Retreat | Large Group Getaway on 2