Pet-friendly holiday rentals in Dennis

4.98 out of 5 average rating, 103 reviews

A backyard space is equipped with a fire pit surrounded by four white Adirondack chairs, providing a cozy gathering area. String lights hang overhead, illuminating the outdoor dining table set for a meal. A charming cottage is visible in the background, enhancing the inviting atmosphere.

Home in West Dennis

Sunset Sabbatical Cape Cod

**Newly updated Bathroom for 2026 Season!** Put your feet up and enjoy yourself! Just a 5 minute walk to South Village Beach, you will enjoy everything Cape Cod has to offer. A backyard oasis, complete with Outdoor Shower, beautiful lights, fire pit and grill - you will create family memories here for a lifetime. Updated kitchen with new gas stove, dishwasher and microwave. High-speed WiFi, Roku TVs, luxury pottery barn linens & towels. Small Hypoallergenic Dog(s) allowed with a $50 pet fee.

WalkabilityOutdoor spacesPool

4.98 out of 5 average rating, 248 reviews

A bright bedroom features a spacious bed with colorful blankets and decorative pillows. A variety of sun hats are displayed on the wall, providing a cheerful accent. Natural light enters through the window, illuminating the cozy interior.

Cottage in Dennis

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Welcome to SEAGLASS COTTAGE! 🔸 200 MBPS WIFI 🔸 Steps to sandy beach on a crystal clear pond 🔸 Pet friendly 🔸 Linens & towels are included. Beds will be made 🔸 Swim, fish or use our 2 kayaks & 2 SUP’s 🔸 Bluestone private patio w/waterviews+charcoal BBQ 🔸 Outdoor shower 🔸 Sunroom w waterview 🔸 Washer+dryer 🔸 Fully equipped kitchen w/Carrera marble counter 🔸Gas firepit 🔸Ductless A/C & Heat 🔸Small library of books, didn't finish the book? Take it! 🔸Pet fee $25/day

Outdoor spacesWalkabilityDecor

Guest suite in West Dennis

The exterior of the Victorian home showcases a charming entrance, featuring a central glass door framed by large windows. Vibrant greenery and blooming plants surround the entrance, providing a welcoming atmosphere. A slate pathway leads up to the steps, offering easy access to the porch.

4.94 out of 5 average rating, 169 reviews

*Bass River Victorian Escape* Central A/C*WiFi

Get away from it all. This beautiful Victorian semi-detached home is part of a former sea captain’s house. Refurbished to a high standard, it is light and spacious with 2 bedrooms and 1.5 bathrooms, fully equipped kitchen, and a 3-season porch with its own entrance. The open floor plan, central A/C, W/D in basement, WiFi, smart TV, outdoor BBQ, and shelves filled with books and games for all ages will make your family vacation that much better. Ask about 20% off weeklong stays in Sept & Oct.

Outdoor spacesPetsParking

4.97 out of 5 average rating, 300 reviews

Pet Friendly - Walk to Downtown Dennis Port!

Newly renovated - cozy, clean and bright! PET FRIENDLY! (PRE APPROVAL required) All amenities provided for an enjoyable and relaxing family vacation or quick get-a-way! Three car driveway and private outdoor shower. Five minute walk to Dennis Port Main Street shopping, restaurants, yoga, Pet Salon, and Town playground. South Side Beaches and Ponds just 1 mile away as well as Cape Cod Bike Trail minutes away! Pet friendly beaches in Dennis after Labor Day and before Memorial Day weekends.

PetsWalkabilityBiking

5.0 out of 5 average rating, 368 reviews

A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.

Home in West Yarmouth

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Small 500 sq ft gem . Quintessential Cape Cod cottage WATERFRONT on big Sandy Pond. Step back in time and enjoy being on Cape Cod in your own Camp. Come enjoy this charming cottage with 2 bedrooms and views of the pond throughout. Kayak, fish and swim from your front door. *1 Paddle Bd *4 kayaks- 4 adult/4 child life vests *Gas Fire-pit *Gas Grill *XL outdoor shower *Quiet lakeside hood *Gorgeous marble counters in the new kitchen *Remote control heating & cooling system *WiFi

Outdoor spacesPetsFamily

4.99 out of 5 average rating, 147 reviews

A circular stone fire pit is surrounded by four white Adirondack chairs, offering a cozy gathering spot. Flames flicker above a bed of decorative stones, casting a warm glow. A smooth patio surface extends around the area, enhancing the outdoor experience.

Cottage in West Dennis

5 min walk to beach w/modern amenities

Welcome to west_dennis_rental! Just 5 minutes from the beach, this updated Cape Cod home is perfect for small families seeking a relaxing getaway. Inside, enjoy a remodeled space with modern comforts and cozy charm. Out back, unwind on the patio with a lush lawn and easy-start gas fire pit—great for dinners or s’mores under the stars. Stocked with linens, beach gear, toys, games, Wi-Fi, AC, full kitchen, and grill. Close to Holiday Hill mini golf, ice cream, and seafood shacks!

Outdoor spacesWalkabilityAccess

4.98 out of 5 average rating, 132 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

PetsWalkabilityComfort

4.99 out of 5 average rating, 132 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

☆ Waterfront, located on private saltwater beach (with central location) ☆ Sauna (year-round) ☆ Cozy fireplace (electric) ☆ 3-season patio ☆ 1% donated to Cape nonprofits ☆ 2 Kayaks & 2 Paddle boards ☆ Outdoor fire pit & charcoal grill ☆ Ample workspace ☆ Dog Friendly ☆ Washer/dryer ☆ 2 King Beds with 50" TVs in bedrooms ☆ Outdoor shower (open May through fall) ☆ Beach chairs provided ☆ Linens, all towels provided ☆ 10min from bay or ocean beach ☆ 15min MV & Nantucket ferries

Outdoor spacesPetsGrill

A loft space features three full beds and three twin beds, suspended from the ceiling by thick manila rope. Blue bedding adds a coastal touch, while the light wood floor complements the airy atmosphere. Large windows provide natural light, enhancing the open design.

5.0 out of 5 average rating, 103 reviews

Cozy Family Retreat Sleeps 14 Pets Fire Pit

There are two homes that combine to create the picture-perfect Cape getaway for your extended family! As you pull onto the shell and stone driveway, you are welcomed by planters adorning every first-floor window. Both structures have been completely renovated in 2021/22. No detail was spared - from the countertops reminiscent of the sea and surf, the finest fixtures and faucets, wicker and rope decor bringing all the coastal vibes in, and nautical details around every turn.

WalkabilityPetsCondition

A charming Cape Cod house is presented, featuring a light grey exterior and a sloped roof. A white picket fence surrounds the front yard, adorned with neatly trimmed bushes. A stone pathway leads to the front door, framed by windows and a symmetrical layout.

4.86 out of 5 average rating, 226 reviews

Lovely! 4Bed 3baths Walk to Beach DennisPort

Dennisport! Excellent location! Great for groups and families! Easy walk to 3 public Beaches with the warm waters of Nantucket sound! This lovely home is fully equipped, comfortably sleeps 8 with 4 bedrooms, 3 baths, outdoor shower and al fresco dining on deck or porch. A mile to downtown where you'll find great restaurants and cafes. The space is designed for comfort and convenience and exploring the Cape from this Dennisport home is easy due to it's central location.

PetsOutdoor spacesHiking

4.99 out of 5 average rating, 155 reviews

A cozy studio space showcases a grey sofa with decorative cushions, positioned beside a small table featuring a fan. The kitchenette is visible in the background, equipped with white cabinetry and essential appliances. Natural light filters through a window, illuminating the warm and welcoming interior.

Flat in West Dennis

The Cape Cod Perch at West Dennis Beach Studio Apt

Take it easy at this unique and tranquil getaway just a short walk from three Nantucket Sound beaches. This 300-square-foot studio apartment on the second floor of our home. With a brand new Weber grill, picnic table, and fire pit, there is plenty of outside living. Trotting Park, South Village, and West Dennis Beaches are all walkable. Enjoy food from Sandbar, Swan River Seafood, Chapin's, Cleat & Anchor, & Bandera's Market in the summer. Call off season.

Outdoor spacesWalkabilityGetting around

4.86 out of 5 average rating, 113 reviews

An outdoor space features a cozy seating area with blue cushions surrounding a fire table. A dining table is set nearby, accompanied by a grill and outdoor kitchen. String lights provide subtle illumination, enhancing the space for gatherings. A television is mounted on the wall.

Home in East Dennis

Speakeasy Bar • Hot Tub • PetsOK• Close2Mayflower

Spacious 4-bedroom Cape Cod retreat just five minutes from Mayflower Beach, with a private hot tub, fully fenced backyard, outdoor kitchen, and a speakeasy-style game room with custom bar and pool table. Sleeps large groups in comfort, welcomes families and pets, and offers an optional private chef and in-home dining experience. Dining for 10, a 65" HDTV with streaming, and a dedicated workspace make it as easy to gather as it is to unwind.

WalkabilityOutdoor spacesCheck-in

Popular amenities for Dennis pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 138 reviews

A living room area presents a grey sofa adorned with patterned cushions, accompanied by a woven coffee table. A standing lamp provides light beside a simple side table with decor. The soft, green walls are complemented by dark curtains and framed artwork.

Home in Yarmouth

Modern Beach + Pond Getaway | Heart of Cape Cod

Outdoor spacesPetsAmenities

4.93 out of 5 average rating, 164 reviews

Home in Brewster

4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC

PetsOutdoor spacesAccuracy

The beachfront property is showcased against a vibrant sunset sky, with gentle waves lapping the sandy shore. Steps built into the rocky landscape lead down to the beach, while coastal homes are visible in the background, creating a serene and inviting setting.

4.83 out of 5 average rating, 105 reviews

Gorgeous Modern Ocean-Front Cottage With Hot Tub

PetsWalkabilityFamily

A charming home features a light grey exterior with a dark shingled roof and two dormer windows. A front yard with green grass is accented by a wooden fence. Two black Adirondack chairs are positioned invitingly on the lawn.

4.78 out of 5 average rating, 111 reviews

Sandy Feet Retreat

PetsOutdoor spacesBathroom

The living area features a cozy arrangement of blue sofas surrounding a coffee table, with artwork on the walls and soft lighting. A fire pit shines brightly in the backyard, where guests gather under string lights, creating a welcoming atmosphere. A spacious bedroom includes a neatly made bed with beach-themed decor and a fan overhead. A storage area displays bicycles, demonstrating available amenities for outdoor activities.

4.92 out of 5 average rating, 425 reviews

★ 0.4mi Beach &Village ★Firepit & Fireplace★ Bikes

WalkabilityPetsDecor

5.0 out of 5 average rating, 231 reviews

An outdoor patio area is illuminated softly at dusk, featuring a dining set with a table and several chairs arranged on a patterned rug. Lush greenery and flowering plants surround the space, while lanterns provide a gentle glow, enhancing the tranquil environment.

Home in Marstons Mills

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

PetsWalkabilityDecor

4.95 out of 5 average rating, 320 reviews

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

Slate House - a modern waterfront getaway

Outdoor spacesWalkabilityQuiet

4.97 out of 5 average rating, 120 reviews

A charming living room features a comfortable sofa with blue and white patterns, situated beside a warm gas fireplace. Sunlight filters through windows, illuminating a coffee table with a tray and snacks. Bookshelves adorned with decorative items line the walls, enhancing the cozy ambiance.

Home in Harwich Port

Pebbles-romantic cottage for two!

WalkabilityOutdoor spacesLayout

Pet-friendly home rentals with a pool

4.89 out of 5 average rating, 101 reviews

A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.

Villa in Wareham

Perfect Farmhouse Discounted for Draft Day!

PetsOutdoor spacesAmenities

4.89 out of 5 average rating, 332 reviews

A view overlooking a well-maintained pool surrounded by green grass, with beach access visible in the distance. The landscape features a mix of trees and charming houses, set against a clear blue sky and tranquil water.

Home in Plymouth

Ocean Side, Amazing View, close to town/beach, Spa

PetsOutdoor spacesNearby

4.92 out of 5 average rating, 52 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

WalkabilityOutdoor spacesTV

5.0 out of 5 average rating, 10 reviews

Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Outdoor spacesHospitalityAccuracy

4.89 out of 5 average rating, 9 reviews

Flat in Dennis Port

Deluxe Double Room | Full Studio w/ Kitchenette

PetsValueAccuracy

4.97 out of 5 average rating, 30 reviews

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

PetsWalkabilityHospitality

5.0 out of 5 average rating, 42 reviews

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

Home in Harwich

Harwich Haven: Pool & Fire Pit

PetsWalkabilityCheck-in

Superhost

The outdoor area features a private in-ground plunge pool surrounded by a patio. Comfortable lounge chairs and a dining set are positioned nearby under a patio umbrella. A screened-in porch with multiple seating options adds to the versatility of the space, while lush greenery provides a natural backdrop.

Home in Brewster

4.81 out of 5 average rating, 27 reviews

In-Ground Plunge Pool Dog Friendly!

PetsOutdoor spacesAir conditioning

Private, pet-friendly home rentals

4.97 out of 5 average rating, 140 reviews

A cozy living area features a sectional sofa and a single accent chair in soft blue tones. A glass coffee table sits on a plush area rug, with a gas fireplace integrated into a brick mantel. Natural light enters through large windows, enhancing the warm ambiance.

Cottage in Yarmouth

Walk 7/10 mile to Beaches *Dog Friendly*

Outdoor spacesPetsDecor

5.0 out of 5 average rating, 21 reviews

Dennis Port | 5-Min to Glendon Beach

Outdoor spacesPetsHospitality

Superhost

Home in Yarmouth

4.83 out of 5 average rating, 6 reviews

3 beds 2 bath cape house

PetsAccuracyQuiet

4.96 out of 5 average rating, 45 reviews

Home in South Dennis

3 BR dream cottage minutes from Cape Cod beaches!

Outdoor spacesWalkabilityBiking

4.96 out of 5 average rating, 70 reviews

A sunlit living area features large windows that provide views of the surrounding trees and nearby pond. A cozy circular chair invites relaxation, while a small dining table with black chairs offers a spot for meals. Green plants add a natural touch to the decor.

Home in South Dennis

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

PetsWalkabilityParks

4.89 out of 5 average rating, 79 reviews

The exterior of a seaside cottage is presented, featuring white siding and blue shutters. A clear pathway leads to the front steps, surrounded by well-maintained landscaping, including shrubs and a tree. A lamp post stands near the entrance, enhancing the home's welcoming appearance.

Cottage in Dennis

Escape to the Cape! Close to Mayflower Beach!

PetsOutdoor spacesSleep quality

4.97 out of 5 average rating, 32 reviews

This newly renovated kitchen features an open-concept layout with bright green walls and ample natural light. A spacious kitchen island with seating for four is complemented by stainless steel appliances and white cabinetry. Access to the outdoor area is available through the door on the right.

Home in East Dennis

~2mi. to Mayflower/Bayside Beaches, BIG Yard

PetsWalkabilityLocation