Find short term rentals in Orleans, MA at the best prices
628 available short term rental offers
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Best Short term and Weekly rentals in Orleans, MA
Orleans, MA
03/08 – 07/08
$884/nighttotal: $3536 (4 )
Wellfeet Retreat
3 3
apartment , Eastham
This Wellfleet flat offers proximity to Cahoon Hollow Beach, bayside waters for swimming, and downtown Wellfleet's restaurants, galleries, and shops, with the Wellfleet Drive-In Theater also nearby. This property accommodates up to six guests, featuring three bedrooms, one bathroom, a fully equipped kitchen, air conditioning, a garden with a grill and fire pit, and an in-home washer and dryer.
Orleans, MA
25/06 – 30/06
$695/nighttotal: $3475 (5 )
Peaceful Waterfront Cottage Escape
2 2
apartment , Eastham
This waterside cottage in Eastham offers direct access to Town Cove, with the Cape Cod National Seashore, bay and ocean beaches, local eateries, and cycle routes all within easy reach. This two-bedroom, two-bathroom holiday home accommodates four guests and includes a private dock with complimentary kayaks and canoes, a shared patio with a fire pit, an enclosed dog area, and the Xplorie programme providing $750 daily for attractions such as Island Cruises and Whale Watch.
Orleans, MA
03/08 – 07/08
$943/nighttotal: $3772 (4 )
Oakwood Trail Cottage | Eastham Home On Cape Cod Rail Trail With Great Deck
4 3
apartment , Eastham
This North Eastham flat offers direct access to the Cape Cod Rail Trail and is situated just 4.8 kilometres from Great Pond Beach and Nauset Light Beach, with Marconi Beach 6.4 kilometres away. This 138 square metre dwelling accommodates up to seven guests, featuring four bedrooms, two bathrooms, a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, complimentary WiFi, and an outdoor shower, ideal for exploring the surrounding area.
9.8 202 reviews
Orleans, MA
25/06 – 30/06
$621/nighttotal: $3105 (5 )
The Whalewalk Inn & Spa
1 2
B&B , Eastham
The Whalewalk Inn & Spa is situated in Eastham, just a short drive from Coast Guard Beach and the Wellfleet Drive-In, making it a great base for exploring the area. The inn has received excellent ratings for its location, cleanliness, and overall guest experience. The inn offers a range of comfortable rooms, each with its own private bathroom and modern amenities. Guests can enjoy a relaxing atmosphere with a hot tub, a garden, and a terrace, as well as a range of activities including swimming, tennis, and spa treatments.
10 11 reviews
Orleans, MA
25/06 – 30/06
$491/nighttotal: $2455 (5 )
Cozy Apartment In A Quiet Wooded Neighborhood, Just 2 Miles From Nauset Beach.
1 2
apartment , Orleans
This one-bedroom flat is situated in East Orleans, just a short distance from the beautiful Nauset and Skaket beaches, making it perfect for exploring the Cape Cod coastline. It has received excellent ratings from previous guests, making it a popular choice for travellers. This comfortable home away from home offers all the amenities you need for a relaxing stay, including air conditioning and the option to bring your pet. You can enjoy the nearby attractions like the Orleans Bowling Center, Cape Escape Adventure Golf, and the Cape Cod National Seashore.
Orleans, MA
25/06 – 30/06
$1052/nighttotal: $5260 (5 )
Getaway Near Bakers Pond & Beaches 2422
4 2
apartment , Orleans
This Orleans holiday home offers deeded access to Bakers Pond and is conveniently located within 1 kilometre of the A10 highway for exploring Cape Cod, with downtown Orleans and its shops, restaurants, and the Cape Cod Baseball League just a short distance away. This four-bedroom, three-bathroom property accommodates up to eight guests and features an open-plan living area, a sunroom with a sofa bed, a primary bedroom suite with deck access, a finished basement with laundry facilities, and a private garden with a deck and barbecue, all while being a short walk from Bakers Pond's sandy beaches.
9.9 26 reviews
Orleans, MA
25/06 – 30/06
$1193/nighttotal: $5965 (5 )
Close To Town And Nauset Beach, Ev Charger, Air Conditioning, Outdoor Shower.
1 2
apartment , Orleans
This apartment is located in Orleans, just a short walk from Baker's Pond and Nickerson State Park, and within easy reach of Nauset and Skaket Beaches. It enjoys a tranquil wooded setting, close to nature and popular beaches, and has received excellent ratings for its location, cleanliness, and overall experience. The property offers 279 square metres of space, comfortably accommodating up to 10 guests across multiple bedrooms. Enjoy modern amenities including central air conditioning, a well-equipped kitchen, a spacious patio with an outdoor shower and fire pit, and a shared landscaped yard.
9.8 8 reviews
Orleans, MA
25/06 – 30/06
$651/nighttotal: $3255 (5 )
Eastham Bungalow
1 2
apartment , Eastham
This Eastham cottage, ideally situated between the bay and ocean beaches, offers easy access to the Cape's best beaches and towns; precise distances are not specified. The two-bedroom, one-bathroom property sleeps four, boasting a full kitchen, air conditioning, a screened-in porch with a smart TV, outdoor shower, deck, and ample garden space with Adirondack chairs and a picnic table.
10 1 review
Orleans, MA
03/08 – 07/08
$916/nighttotal: $3664 (4 )
Peaceful Retreat On Chilton Lane
2 3
apartment , Brewster
This Brewster apartment is conveniently located near Cape Cod beaches and attractions such as the Cape Cod Inflatable Park, offering easy access to other Cape Cod destinations. The 87-square-metre (936 square feet) self-catering flat features two bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, balcony, free Wi-Fi, a swimming pool, fitness centre, and concierge service; on-site amenities also include a water park, indoor pool, and hot tub.
Orleans, MA
25/06 – 30/06
$491/nighttotal: $2455 (5 )
60 M² Cottage ∙ 1 Bedroom ∙ 2 Guests
1 2
cottage , Eastham
This Eastham holiday let is situated on Town Cove, providing direct water access and a private dock, with Rock Harbor Beach and the Cape Cod Rail Trail within 3.2 kilometres. This 60 square metre bungalow accommodates two guests with one bedroom and one bathroom, featuring air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and complimentary daily tickets to local attractions through the Xplorie partnership, alongside provided kayaks and canoes.
9.7 34 reviews
Orleans, MA
25/06 – 30/06
$624/nighttotal: $3120 (5 )
Inn At The Oaks
1 2
B&B , Eastham
This Eastham bed and breakfast is situated just 1.6 kilometres from Coast Guard Beach and a 5-minute drive from the Salt Pond Visitor’s Center, offering easy access to the Cape Cod National Seashore’s beautiful beaches and natural landscapes. The guesthouse has received very good ratings from previous guests and is considered to have an excellent location. The property features a backyard with an outdoor patio, fire pit, and wraparound porch, ideal for relaxing and enjoying the fresh Cape Cod air. Each room includes a flat-screen cable TV and private bathroom, and a continental breakfast is served each morning, with refreshments available in the afternoon.
9.8 10 reviews
Orleans, MA
03/08 – 07/08
$1026/nighttotal: $4104 (4 )
Walk To The Beach At Little Pleasant Bay From This Newly Decorated Cottage!
1 3
apartment , Orleans
This apartment is conveniently located in Orleans, just 1.6km from the beautiful beaches of Cape Cod and within a 5km radius of Captain's Cove Golf Course and Captains Golf Course. The property has received excellent user ratings, making it a popular choice for travellers. The apartment comfortably sleeps six guests and features a well-equipped kitchen with a fridge, microwave, and dishwasher. Guests can enjoy the on-site barbecue grills, the terrace or balcony, and the garden, as well as the convenience of parking, air conditioning, and internet access.
Best family friendly Orleans, MA Short term rentals
Among the 628 accommodations in Orleans, MA, here are the 4 best family friendly rentals
9.6 23 reviews
Orleans, MA
25/06 – 30/06
$2010/nighttotal: $10050 (5 )
Exceptional Mid-cape Oasis With Many Amenities!
4 2
apartment , Harwich
This apartment is ideally located in Harwich, just 16km from the charming town of Chatham and 48km from Provincetown. The property has excellent user, location, and cleanliness ratings, indicating a high-quality stay. This spacious home has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The apartment offers a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and parking, ensuring a relaxing and enjoyable stay.
10 4 reviews
Orleans, MA
25/06 – 30/06
$1450/nighttotal: $7250 (5 )
Charming Retreat Near The Ocean With W/d, Games, & Trails
5 2
apartment , Eastham
This five-bedroom Eastham holiday home offers direct access to the Cape Cod National Seashore and is a short walk to the beach and the Cape Cod Rail Trail, ideal for cycling and walking. This 190 square metre property accommodates up to ten guests with four bathrooms, a well-equipped kitchen including a dishwasher, and a screened porch, alongside outdoor games and a deck with a grill for entertainment.
Orleans, MA
25/06 – 30/06
$1410/nighttotal: $7050 (5 )
New 2026 Charming Home Just Over A Mile To Coast G
1 2
apartment , Eastham
This Eastham holiday let offers a prime location, a short walk from the Cape Cod National Seashore visitor centre and approximately 2.4 kilometres from Coast Guard Beach. This family-friendly holiday home accommodates eight guests across four bedrooms and features two bathrooms, air conditioning, a garden, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
This upper-level Cape Cod cottage in East Orleans offers direct, walkable access to Nauset Beach, eliminating parking issues, and is a 1.6 to 2.4 kilometre drive from the Cape Cod Rail Trail. This 103 square metre flat, accommodating up to six guests across three bedrooms and one bathroom, features a kitchen with a fridge and microwave, air conditioning, a terrace/balcony, and is situated a short walk from Orleans shops, dining, and attractions like the Orleans Bowling Centre.
Best Orleans, MA lodging with a balcony
9.6 11 reviews
Orleans, MA
03/08 – 07/08
$1426/nighttotal: $5704 (4 )
Book Eastham, Plenty Of Room For Entire Family!
3 3
apartment , Eastham
This Eastham apartment is situated in a quiet residential area, 1.6 kilometres from Nauset Light Beach and close to bayside beaches suitable for families. This 167 square metre residence accommodates up to six guests across three bedrooms and two bathrooms, featuring a fully equipped kitchen, a separate dining room, a downstairs entertainment area, and extensive outdoor space with a gas grill and firepit, all supported by WiFi and parking for four vehicles.
9.2 50 reviews
Orleans, MA
25/06 – 30/06
$761/nighttotal: $3805 (5 )
Ship's Knees Inn
1 2
B&B , Orleans
The Ship's Knees Inn is a charming bed and breakfast located just a five-minute walk from Nauset Beach in Orleans, offering easy access to the beautiful sandy shores and the Cape Cod Rail Trail. The inn has received excellent ratings for its cleanliness, location and overall experience. The rooms are decorated in a traditional Cape Cod style, creating a welcoming and authentic atmosphere. Guests can enjoy a continental breakfast, relax on the terrace with a fire pit, take a dip in the seasonal pool, or explore the nearby Cape Cod Museum of Natural History.
10 1 review
Orleans, MA
25/06 – 30/06
$479/nighttotal: $2395 (5 )
Renovated 2nd-floor Corner Unit, New Interiors. Beach, Parking Passes On Us.
1 2
apartment , Brewster
This recently renovated one-bedroom flat is located within the Ocean Edge resort in Brewster, offering convenient access to Cape Cod Beaches and Nickerson State Park, just 1.6 kilometres away. This apartment accommodates up to four guests with a queen bed and a sleeper sofa, featuring a fully equipped kitchen, air conditioning, a balcony, garden access, and dedicated parking, with beach chairs and towels provided for your use.
Orleans, MA
03/08 – 07/08
$1059/nighttotal: $4236 (4 )
Gorgeous Woodland Home With Deck & Firepit - Walk To Ocean Bluffs & Rail Trail
3 3
apartment , Eastham
This Eastham residence, a detached house, offers a secluded woodland setting with wildlife and is situated less than 1 kilometre from ocean bluffs and just over 1.6 kilometres from Nauset Light Beach, also being conveniently located half a kilometre from the Cape Cod Rail Trail. This spacious 218 square metre property boasts three bedrooms and three bathrooms, accommodating up to four guests, and features unique reclaimed American chestnut beams, expansive outdoor space including a deck and firepit, a sunroom, and central air conditioning downstairs with mini-splits upstairs.
Frequently Asked Questions about short term rentals in Orleans, MA
What are the best short term rentals in Orleans, MA?
This Orleans cottage is located in a quiet neighbourhood, just a short distance from the popular Skaket Beach. This property offers accommodation for up to five guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen, a three-season sunroom, a finished basement with a ping pong table, a private deck with a gas grill, and an enclosed outdoor shower.
Orleans, MA
25/06 – 30/06
$702/nighttotal: $3510 (5 )
Peaceful Waterfront Cottage Escape
2 2
cottage , Eastham
This Eastham holiday home is located on Town Cove, offering direct water access and a private dock, with the Cape Cod National Seashore just 1.4 kilometres away and the Cape Cod Rail Trail 1.5 kilometres distant. This two-bedroom, two-bathroom cottage spans 121 square metres, accommodates four guests, and includes a kitchen with a fridge and microwave, air conditioning, Wi-Fi, parking, and complimentary daily tickets to local attractions through the Xplorie partnership.
9.8 9 reviews
Orleans, MA
25/06 – 30/06
$702/nighttotal: $3510 (5 )
Relax And Refresh In Eastham
1 2
apartment , Eastham
This Eastham flat offers a prime location, a mere 800 metres from First Encounter Beach and 1.6 kilometres from Coast Guard Beach. This newly available coastal retreat sleeps up to six guests across two bedrooms and a loft, featuring an open-plan living, dining, and kitchen area with air conditioning, Wi-Fi, and off-street parking.
Orleans, MA
25/06 – 30/06
$386/nighttotal: $1930 (5 )
Beautifully Renovated Second-floor Condo
1 2
apartment , Brewster
This newly renovated one-bedroom flat in Brewster is located within the Ocean Edge Resort, offering proximity to the Cape Cod Bay shoreline. This accommodation provides a queen bed and sleeper sofa for up to four guests, a fully equipped kitchen with new appliances, a recently updated bathroom, and year-round comfort with heating and air conditioning, all complemented by complimentary parking.
Best Orleans, MA lodging with laundry available
9.4 8 reviews
Orleans, MA
25/06 – 30/06
$742/nighttotal: $3710 (5 )
Spacious Harwich Haven Near Round Cove (1116)
3 2
apartment , Harwich
This detached house in Harwich is located on a quiet cul-de-sac, 800 metres from Round Cove on Pleasant Bay, offering convenient access to Chatham and Orleans. The property features four bedrooms accommodating up to eight guests, a well-equipped kitchen, a TV room, a large living room with deck access, a garden with an enclosed outdoor shower, and a gas barbecue, with nearby activities including sailing, surfing, fishing, and cycling.
9.5 4 reviews
Orleans, MA
25/06 – 30/06
$750/nighttotal: $3750 (5 )
Large Family Home & Yard: Your Cape Cod Getaway
1 2
apartment , Eastham
This Eastham holiday home enjoys a superb location, less than 1.6km from the Cape Cod Rail Trail, Fort Hill Trail, and Great Pond Beach, with First Encounter Beach (3.2km) and Nauset Light Beach (6.4km) also within easy reach. Sleeping eight, this three-bedroom, two-bathroom property boasts a full kitchen, air conditioning, Wi-Fi, a private garden with barbecue and fire pit, plus bikes and beach toys; a unique basement 'Connie's Pub' adds a quirky touch.
Orleans, MA
25/06 – 30/06
$1005/nighttotal: $5025 (5 )
Harwich Escape – Deck, Firepit & Near Beaches
3 2
apartment , Harwich
This Harwich Port flat is situated 0.7 kilometres from Pleasant Road beach, with Harwich Port's shops and eateries a short distance away, and offers convenient access to the Cape Cod Rail Trail for cycling and walking. This property accommodates up to eight guests across three bedrooms and two bathrooms, boasting a garden with a deck, patio, gas grill and firepit, an outdoor shower, and a well-equipped kitchen with full-size appliances, plus air conditioning and Wi-Fi for comfort.
Orleans, MA
25/06 – 30/06
$602/nighttotal: $3010 (5 )
Cozy Cottage By Molls Pond 2409
2 2
apartment , Eastham
This two-bedroom cottage is situated in a tranquil Eastham neighbourhood, offering swift access to Route 6 and proximity to the Atlantic and Cape Cod Bay beaches, with Molls Pond just 400 metres away for fishing and kayaking. This holiday let accommodates up to four guests and features a garden, outdoor shower, and a porch with dining facilities, alongside an open-plan living area with a television and air conditioning, plus a fitness centre for guest use.