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Best Vacation rentals and Airbnb offers in Orleans, MA
9.4 20 reviews
Orleans, MA
08/03 – 08/07
$1675/nighttotal: $6700 (4 )
Barley Breeze
3 3
house , Orleans
This East Orleans vacation home is conveniently located 2.6 miles from Cape Cod Beaches and 2.9 miles from Nauset Inlet, offering easy access to Orleans Bowling Center and Nauset Beach within a 6-mile radius. This 2010-square-foot house features three bedrooms, three bathrooms, and accommodates eight guests, boasting a fully equipped kitchen, in-house laundry, a balcony, a garden, and parking.
9.4 20 reviews
Orleans, MA
08/03 – 08/07
$1452/nighttotal: $5808 (4 )
Two-story Home W/new Kitchen, Washer/dryer, Large Yard, & Pool Table
3 3
apartment , Orleans
This Cape Cod retreat is located in East Orleans, a short drive from downtown Orleans, and offers direct access to Pochet Bay for kayaking and canoeing. This 2010 square foot rental features 3 bedrooms, 3 bathrooms, and can accommodate up to 8 guests, with a newly remodeled kitchen, a pool table, and an outdoor shower.
Orleans, MA
06/25 – 06/30
$752/nighttotal: $3760 (5 )
Getaway Near Bakers Pond & Beaches 2422
4 2
apartment , Orleans
This Orleans house offers a private neighborhood setting with deeded access to Bakers Pond's clear waters and sandy beaches, located minutes from downtown Orleans' shops and restaurants, and with quick highway access for exploring Cape Cod. This 4-bedroom, 3-bathroom rental sleeps 8 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, driveway parking for 4 cars, and a finished basement with laundry.
9.8 8 reviews
Orleans, MA
06/25 – 06/30
$465/nighttotal: $2325 (5 )
Eastham Bungalow
1 2
apartment , Eastham
This Eastham cottage rental, ideally situated between the bay and ocean beaches, offers easy access to Cape Cod's renowned beaches and towns. The two-bedroom, one-bathroom home sleeps four and features a full kitchen, gas grill, screened porch with smart TV, outdoor shower, deck, and ample space for beach gear; two smart TVs and a picnic table are also provided.
Orleans, MA
06/25 – 06/30
$434/nighttotal: $2170 (5 )
Relaxing Eastham Retreat With Waterfront Views
2 2
apartment , Eastham
This 2-bedroom, 1-bathroom cottage, Bell Buoy, is situated directly on Town Cove in Eastham, offering waterfront access with a private dock and proximity to the Cape Cod National Seashore, bay and ocean beaches, restaurants, and bike trails. Enjoy a split-level design with a gas fireplace, a private deck with cove views for grilling, a shared patio with a fire pit, an enclosed dog area, and complimentary daily tickets through Xplorie valued at $750 for activities like Island Cruises and Whale Watch tours.
9.4 24 reviews
Orleans, MA
06/25 – 06/30
$669/nighttotal: $3345 (5 )
Areys Pond Point
4 2
house , Orleans
This Orleans beachfront home, located on Areys Pond Point, is 8.7 miles from Nauset Lighthouse and 15 miles from Wellfleet Bay Wildlife Sanctuary, offering stunning ocean views. This 1,380-square-foot house features four bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, free Wi-Fi, and a private entrance, comfortably accommodating families or groups.
9.0 21 reviews
Orleans, MA
06/25 – 06/30
$510/nighttotal: $2550 (5 )
West-facing Pure Waterfront Home In Orleans, Overl
4 2
apartment , Orleans
This Orleans vacation home boasts 2+ waterfront acres with Arey's Pond access, situated four miles from Nauset and Skaket Beaches and within one mile of two freshwater swimming lakes. This four-bedroom, two-bathroom house sleeps eight, features a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, free parking for four cars, and offers extraordinary privacy with access to 11+ acres of conservation land for nature walks.
8.3 2671 reviews
Orleans, MA
06/25 – 06/30
$464/nighttotal: $2320 (5 )
The Mansion At Ocean Edge Resort & Golf Club
1 2
resort , Brewster
The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. The resort has excellent ratings for location, cleanliness, and overall experience. The resort offers spacious villas with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a private beach, indoor and outdoor pools, a golf course, tennis courts, a kids' club, multiple dining options, and a fitness center.
Orleans, MA
06/25 – 06/30
$343/nighttotal: $1715 (5 )
New Brewster Condo Near Beach
1 2
apartment , Brewster
This condo is located in the Ocean Edge Resort community, offering convenient access to Brewster's beaches, the Cape Cod Rail Trail, and local shops and restaurants. This apartment features 1 bathroom, accommodates up to 4 guests, and includes a modern kitchen with a dishwasher, air conditioning, and a private patio with golf course views, perfect for enjoying Cape Cod.
9.8 111 reviews
Orleans, MA
06/25 – 06/30
$459/nighttotal: $2295 (5 )
Cozy Cape Condo Minutes From Brewster Beaches
1 2
apartment , Brewster
This Brewster condo, located on the Ocean Edge Resort Golf Course, offers easy access to Breakwater Beach and Crosby Landing Beach, plus proximity to restaurants like The Brewster Fish House. The 2-bedroom, 2-bathroom unit sleeps 6, features a fully equipped kitchen, patio overlooking the golf course, beach gear, and a 55-inch 4K Samsung TV with streaming services.
Orleans, MA
06/25 – 06/30
$438/nighttotal: $2190 (5 )
Serene Retreat With Cove Views
1 2
cottage , Eastham
This waterfront cottage in Eastham offers direct access to Town Cove, with the Cape Cod National Seashore 4 miles away, Rock Harbor Beach 2 miles away, and the Cape Cod Rail Trail 1.5 miles away. This 650-square-foot rental accommodates two guests with one bedroom and one bathroom, featuring a private deck with a gas grill, keyless entry, and complimentary linens, plus $750 in daily free tickets to local attractions through Xplorie.
This upper-level Cape Cod cottage in East Orleans offers direct, walkable access to Nauset Beach, putting you steps from the sand with Orleans' shops and dining a short drive away. This family-friendly rental spans 1110 square feet, featuring 3 bedrooms to accommodate up to 6 guests, air conditioning, a kitchen equipped with a fridge and microwave, and provided beach towels and chairs.
Best Orleans, MA vacation rentals with a balcony
Orleans, MA
06/25 – 06/30
$329/nighttotal: $1645 (5 )
New Cape Cod Condo Near Beaches
1 2
house , Brewster
This Cape Cod condo is located in Brewster, 12 miles from Nauset Lighthouse and 13 miles from Wellfleet Bay Wildlife Sanctuary. This 80 square feet rental sleeps 7 guests and features air conditioning, a full kitchen with a dishwasher and microwave, a fireplace, a private terrace, and complimentary parking and WiFi.
9.8 6 reviews
Orleans, MA
06/25 – 06/30
$1185/nighttotal: $5925 (5 )
Newly Built, Bayview House Steps From The Beach With Spacious Deck, W/d & Grill
2 2
apartment , Eastham
This newly constructed Cape Cod-style residence in North Eastham offers direct access to a private bay beach and is located within minutes of ocean beaches, the Cape Cod Rail Trail, and the Cape Cod National Seashore. This 1600 square foot vacation rental accommodates up to four guests with two king bedrooms and a den with a full-size bed, featuring a full kitchen, air conditioning, a terrace, a finished basement with an Xbox One, and a private outdoor shower.
Orleans, MA
08/03 – 08/07
$758/nighttotal: $3032 (4 )
Gorgeous Woodland Home With Deck & Firepit - Walk To Ocean Bluffs & Rail Trail
3 3
apartment , Eastham
This Eastham residence offers a woodland escape, situated less than 1 mile from ocean bluffs and just over 1 mile from Nauset Light Beach, with the Cape Cod Rail Trail a half-mile walk away. This 3-bedroom, 3-bathroom house spans 2350 square feet and accommodates up to 4 guests, featuring a fenced yard with a deck and patio, central air conditioning, and a kitchen equipped with a fridge, microwave, and dishwasher.
10 1 review
Orleans, MA
06/25 – 06/30
$343/nighttotal: $1715 (5 )
Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us.
1 2
apartment , Brewster
This one-bedroom condo is located within the Ocean Edge resort in Brewster, offering resort amenities and convenient access, approximately 0.5 miles from Nickerson State Park and close to Cape Cod Beaches. This newly renovated unit accommodates up to 4 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a private balcony, garden access, and dedicated parking, with beach chairs, towels, and an umbrella provided for your use.
Guest-Favorite Family Vacation Rentals in Orleans, MA
These family-friendly vacation rentals in Orleans, MA offer plenty of room to spread out near local beaches.
Orleans, MA
06/25 – 06/30
$403/nighttotal: $2015 (5 )
121 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests
2 2
cottage , Eastham
This Eastham cottage, Mate's Quarters, offers waterfront views on Town Cove, with convenient access to the Cape Cod National Seashore (1.4 miles to Fort Hill Trail), Rock Harbor Beach (2.0 miles), local restaurants, and the Cape Cod Rail Trail (1.5 miles). This two-story rental features 2 bedrooms, 2 bathrooms, and sleeps 4 guests, with amenities including air conditioning, internet, a full kitchen with a fridge and microwave, parking, and a private dock with kayaks and canoes, plus a shared patio with a fire pit and complimentary daily tickets through Xplorie.
Orleans, MA
06/25 – 06/30
$579/nighttotal: $2895 (5 )
Cape Escape Harwich
1 2
apartment , Harwich
This 3-bedroom house in Harwich offers a spacious retreat for up to 8 guests, conveniently located a short drive from Harwich and Chatham, and within close proximity to Wequassett Inn, Wychmere, and Chatham Bars Inn. The accommodation features a finished basement with bonus sleeping space, a large yard with a deck and outdoor shower, and complimentary baby gear, beach chairs, and towels for a family-friendly stay.
9.6 23 reviews
Orleans, MA
06/25 – 06/30
$1438/nighttotal: $7190 (5 )
Exceptional Mid-cape Oasis With Many Amenities!
4 2
apartment , Harwich
This Harwich rental is located in central Cape Cod, just minutes from a pond or bay for swimming and a short drive from many Cape beaches. It has excellent user, location, and cleanliness ratings. This four-bedroom, three-bathroom home comfortably sleeps eight guests. The home offers a fully fenced yard, a seasonal swimming pool, a hot tub, a fireplace, a dedicated loft office with wifi, plenty of outdoor lounging space, a well-equipped kitchen, and a master bathroom with an indoor spa.
8.0 7 reviews
Orleans, MA
06/25 – 06/30
$436/nighttotal: $2180 (5 )
Light-filled Home Steps From Rail Trail - Near Pon
3 2
apartment , Eastham
This 3-bedroom, 2-bathroom Eastham condo is located on a wooded lot, steps from the Cape Cod Rail Trail, 1 mile from Herring Pond, 2 miles from First Encounter Beach on Cape Cod Bay, and a short drive to Coast Guard Beach within the Cape Cod National Seashore. This vacation rental accommodates up to 6 guests and features a large back deck with a gas grill, a backyard, a Ping-Pong table, an outdoor shower, private laundry, complimentary WiFi, and free parking for 3 vehicles.
Frequently Asked Questions about vacation rentals in Orleans, MA
Which walking or cycling routes are the best in Orléans, MA?
The best walking and cycling route in Orleans is the Cape Cod Rail Trail, which runs for 22 miles along the old railroad line. You can also explore the scenic walking trails at the Nickerson State Park or take a leisurely stroll along the Orleans town center.
What are the best Airbnb and vacation rentals in Orleans, MA?
What sports or outdoor activites can visitors enjoy in and around Orléans, MA?
Orleans is a great place for outdoor activities. You can go swimming, sunbathing, or surfing at Nauset Beach. You can also go kayaking or canoeing on the Pleasant Bay or go fishing in the surrounding waters. If you're looking for something more adventurous, you can try kitesurfing or windsurfing on the bay.
What other towns or cities can be easily accessed from Orléans, MA?
Orleans is ideally located on Cape Cod, so you can easily visit nearby towns like Chatham, Harwich Port, and Dennis. You can also take a short drive to Provincetown, the northernmost town on Cape Cod, or to Hyannis, the main transportation hub for the Cape.
What are the best vacation rentals with a pool in Orleans, MA?
What amenities are commonly available in vacation rentals in Orléans, MA?
Vacation rentals in Orleans typically offer a range of amenities, including kitchens, laundry facilities, Wi-Fi, and outdoor spaces like patios or decks. Some rentals may also have swimming pools, hot tubs, or fireplaces.
What are the best rentals for families and kids in Orleans, MA?
What time of year is best to rent a vacation rental Orléans, MA?
The best time to visit Orleans is during the summer months, from June to August, when the weather is warm and sunny. However, if you're looking for a more peaceful experience, you can visit during the shoulder seasons, spring or fall, when the crowds are smaller and the prices are lower.
What are the best rentals or Airbnbs with a jacuzzi in Orleans, MA?
Orleans is known for its fresh seafood, so you'll find plenty of restaurants serving up lobster rolls, clam chowder, and other seafood dishes. You can also try local specialties like Cape Cod cranberry sauce and Cape Cod oysters.
Destinations nearby
Best Orleans, MA vacation rentals with parking
Orleans, MA
08/03 – 08/07
$433/nighttotal: $1732 (4 )
Cape Cod National Seashore Treehouse Cycle, Swim, Hike Or Kayak With Your Dog
1 3
apartment , Eastham
This Eastham rental is a one-bedroom apartment located in North Eastham's Narrowlands, minutes from Nauset Light Beach and Coast Guard Beach, offering easy access to the Cape Cod Rail Trail. The 1-bedroom unit, situated above a two-car garage, includes a queen bed, daybed, sleeper sofa, full-sized washer/dryer, a 14' x 26' mahogany deck with grill and outdoor shower, accommodating up to four guests and providing convenient access to biking trails and local beaches.
9.7 3 reviews
Orleans, MA
06/25 – 06/30
$856/nighttotal: $4280 (5 )
4 Bedroom Home By Leavetown Vacations
4 2
house , Eastham
This Eastham vacation home is a short walk from Campground Beach and within a few miles of Kingsbury Beach, Wellfleet Bay Wildlife Sanctuary, and Cape Cod National Seashore. The 2,250-square-foot property boasts four bedrooms, three bathrooms, and can comfortably accommodate up to 15 guests, featuring a fully equipped kitchen, Wi-Fi, air conditioning, and a private balcony.
Orleans, MA
08/03 – 08/07
$1084/nighttotal: $4336 (4 )
Screened Porch Overlooking Marsh, Spacious Yard, Patio, Fire Pit, And Close To Beach
2 3
cottage , Eastham
This vacation rental, a cottage in North Eastham, is located 5 miles from South Sunken Meadow Beach and close to the Cape Cod National Seashore. This 700 square foot dwelling accommodates up to 4 guests in 2 bedrooms and features 2 bathrooms, air conditioning, a full kitchen, and on-site laundry, with opportunities for birdwatching and kayaking nearby.
9.6 17 reviews
Orleans, MA
06/25 – 06/30
$817/nighttotal: $4085 (5 )
Beach & Town Walkable:family Friendly Cape Getaway
4 2
apartment , Eastham
This Eastham vacation home is located within 1-2 miles of Campground Beach and Thumpertown Beach on Cape Cod. This four-bedroom, four-bathroom house sleeps eight guests and features a fully equipped kitchen, free Wi-Fi, a private balcony, and outdoor amenities including a garden and grills; limited housekeeping is available.
Check Out Vacation Rentals with a Pool in Orleans, MA
A vacation rental with a pool in Orleans, MA is the ideal way to complement your daily coastal adventures.
9.6 407 reviews
Orleans, MA
06/25 – 06/30
$591/nighttotal: $2955 (5 )
Pleasant Bay Village Resort
1 2
resort , Chatham
The Pleasant Bay Village Resort is located in Chatham, Massachusetts, just 2.5 miles from the Chatham Railroad Museum and an 8-minute drive from the Chatham Lighthouse. This 4-star resort has received excellent user ratings for its location, cleanliness, and overall experience. The resort offers spacious rooms with comfortable furnishings, floral décor, cable TV, a fridge, and a work desk. Guests can enjoy a variety of amenities and activities, including a seasonal outdoor pool, a hot tub, a game room, a children's playground, ping-pong, laundry facilities, and a restaurant.
9.9 44 reviews
Orleans, MA
06/25 – 06/30
$499/nighttotal: $2495 (5 )
Cape Cod's Best! Ocean Edge 2br Billington "A"!
1 2
house , Brewster
This Brewster townhouse, located in the Billington section, offers convenient access to beaches, restaurants, the Cape Cod Baseball League, and the rail trail. The 2-bedroom, 2-bathroom property features a family-friendly layout with a first-floor master bedroom, updated kitchen, private patio overlooking the 9th fairway of a Jack Nicklaus-designed golf course, and accommodates up to 6 guests, boasting amenities such as a swimming pool, Jacuzzi, and fitness center.
Orleans, MA
08/03 – 08/07
$644/nighttotal: $2576 (4 )
Peaceful Retreat On Chilton Lane
2 3
house , Brewster
This Brewster vacation home, located on Chilton Lane, is 1.3 miles from Ellis Landing Beach and 15 miles from Cape Cod Gateway Airport. The 940-square-foot house features two bedrooms, two bathrooms, and accommodates up to nine guests, offering a private garden, swimming pool, jacuzzi, tennis court, and on-site restaurant and bar.
10 1 review
Orleans, MA
08/03 – 08/07
$538/nighttotal: $2152 (4 )
Peaceful Retreat On Chilton Lane
2 3
apartment , Brewster
This Brewster condo rental, located on Chilton Lane, offers easy access to Brewster's beaches, bike trails, and the town center. The 935-square-foot apartment features two bedrooms, two bathrooms, and can comfortably accommodate five guests, boasting a modern kitchen, pondside patio, and access to Ocean Edge Resort amenities (for an additional fee).
Search Coastal Vacation Rentals near Orleans, MA
Discover charming seaside vacation rentals in Orleans, MA near the coast. Browse our favorite coastal picks to find your perfect beach-town match.
Orleans, MA
06/25 – 06/30
$483/nighttotal: $2415 (5 )
Wellfeet Retreat
3 2
apartment , Eastham
Orleans, MA
06/25 – 06/30
$351/nighttotal: $1755 (5 )
60 M² Cottage ∙ 1 Bedroom ∙ 2 Guests
1 2
cottage , Eastham
Orleans, MA
06/25 – 06/30
$522/nighttotal: $2610 (5 )
Relaxing Eastham Retreat With Waterfront Views
1 2
house , Eastham
9.6 16 reviews
Orleans, MA
06/25 – 06/30
$385/nighttotal: $1925 (5 )
Seaside Escape-art-filled 2 Bd On Town Cove
2 2
apartment , Eastham
Discover 5-Star Vacation Rentals in Orleans, MA
Premium waterfront rentals in Orleans, MA combine upscale design with refined service for a truly superior getaway.
10 1 review
Orleans, MA
08/03 – 08/07
$655/nighttotal: $2620 (4 )
Peaceful Retreat On Chilton Lane
2 3
apartment , Brewster
Best Vacation Rentals with a Steam Room in Orleans, MA
Elevate your wellness routine with a vacation rental featuring a sauna in Orleans, MA , ideal for a restorative end to your day.
