Vacation rentals in Head of Hillsborough

27 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals and Airbnb

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best vacation rentals and Airbnb offers in Head of Hillsborough

Cozy Studio Suite, close to walking trail and golfing!! - Head of Hillsborough

Cozy Studio Suite, close to walking trail and golfing!!

Apartment, Head of Hillsborough

Cozy Studio Suite, close to walking trail and golfing!! is a apartment in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Cozy Studio Suite, close to walking trail and golfing!!

Cozy Studio Suite, close to walking trail and golfing!! is a apartment in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $953.

From$136/night
Show
Trailside Inn - Head of Hillsborough

Trailside Inn

Guest House, Head of Hillsborough

Trailside Inn is a guest house in Head of Hillsborough, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

Read more

About Trailside Inn

Trailside Inn is a guest house in Head of Hillsborough, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,228.

From$153/night
Show
Brielle’s River Retreat…..Open Concept Suite - Head of Hillsborough

Brielle’s River Retreat…..Open Concept Suite

Apartment, Head of Hillsborough

Brielle’s River Retreat…..Open Concept Suite is a apartment in Head of Hillsborough, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Brielle’s River Retreat…..Open Concept Suite

Brielle’s River Retreat…..Open Concept Suite is a apartment in Head of Hillsborough, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,610.

From$230/night
Show
PEI cottage, water views, fire pit, A/C, 25 mins from Charlottetown - Donaldston - Head of Hillsborough

PEI cottage, water views, fire pit, A/C, 25 mins from Charlottetown - Donaldston

Cottage, Head of Hillsborough

PEI cottage, water views, fire pit, A/C, 25 mins from Charlottetown - Donaldston is a cottage in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a…

Read more

About PEI cottage, water views, fire pit, A/C, 25 mins from Charlottetown - Donaldston

PEI cottage, water views, fire pit, A/C, 25 mins from Charlottetown - Donaldston is a cottage in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $1,616.

From$231/night
Show

Family-friendly vacation rentals in Head of Hillsborough

Plan a trip with stays that give families more room to spread out.

Beautiful Getaway Plus More! - Head of Hillsborough

Beautiful Getaway Plus More!

Cottage, Head of Hillsborough

Beautiful Getaway Plus More! is a cottage in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Beautiful Getaway Plus More!

Beautiful Getaway Plus More! is a cottage in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,083.

From$298/night
Show
Serendib By St Peters Bay.... ( Three Bedroom Rustic Cottage) - Head of Hillsborough

Serendib By St Peters Bay.... ( Three Bedroom Rustic Cottage)

Cottage, Head of Hillsborough

Serendib By St Peters Bay.... ( Three Bedroom Rustic Cottage) is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and parking. This stay gives travelers a…

Read more

About Serendib By St Peters Bay.... ( Three Bedroom Rustic Cottage)

Serendib By St Peters Bay.... ( Three Bedroom Rustic Cottage) is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,270.

From$324/night
Show
The Heron Nest Prince Edward Island - Head of Hillsborough

The Heron Nest Prince Edward Island

Cottage, Head of Hillsborough

The Heron Nest Prince Edward Island is a cottage in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About The Heron Nest Prince Edward Island

The Heron Nest Prince Edward Island is a cottage in Head of Hillsborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and onsite parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,361.

From$337/night
Show
Ocean view cottage at St. Peter’s Bay - Head of Hillsborough

Ocean view cottage at St. Peter’s Bay

Cottage, Head of Hillsborough

Ocean view cottage at St. Peter’s Bay is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Ocean view cottage at St. Peter’s Bay

Ocean view cottage at St. Peter’s Bay is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,813.

From$402/night
Show

Pet-friendly vacation rentals in Head of Hillsborough

Bring your pet along with stays that welcome four-legged travelers.

Bright and Inviting 3-Bedroom Home Overlooking St. Peter’s Bay - Head of Hillsborough

Bright and Inviting 3-Bedroom Home Overlooking St. Peter’s Bay

Holiday Home, Head of Hillsborough

Bright and Inviting 3-Bedroom Home Overlooking St. Peter’s Bay is a holiday home in Head of Hillsborough, with pet-friendly space, easy beach access, and parking. This stay gives travelers…

Read more

About Bright and Inviting 3-Bedroom Home Overlooking St. Peter’s Bay

Bright and Inviting 3-Bedroom Home Overlooking St. Peter’s Bay is a holiday home in Head of Hillsborough, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,329.

From$333/night
Show
Ocean view cottages with direct beach access - Head of Hillsborough

Ocean view cottages with direct beach access

Cottage, Head of Hillsborough

Ocean view cottages with direct beach access is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Ocean view cottages with direct beach access

Ocean view cottages with direct beach access is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, kitchen, with kitchen, and kids friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,849.

From$550/night
Show
3 bdrm family cottage, short walk to beautiful beach. - Head of Hillsborough

3 bdrm family cottage, short walk to beautiful beach.

Cottage, Head of Hillsborough

3 bdrm family cottage, short walk to beautiful beach. is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About 3 bdrm family cottage, short walk to beautiful beach.

3 bdrm family cottage, short walk to beautiful beach. is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, kitchen, with kitchen, and kids friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $4,440.

From$634/night
Show
Sea Dunes Beach House-2026 Vacation Rental of the Year July11-18,2026 available - Head of Hillsborough

Sea Dunes Beach House-2026 Vacation Rental of the Year July11-18,2026 available

Cottage, Head of Hillsborough

Sea Dunes Beach House-2026 Vacation Rental of the Year July11-18,2026 available is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This…

Read more

About Sea Dunes Beach House-2026 Vacation Rental of the Year July11-18,2026 available

Sea Dunes Beach House-2026 Vacation Rental of the Year July11-18,2026 available is a cottage in Head of Hillsborough, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, kitchen, with kitchen, and kids friendly.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $10,547.

From$1,507/night
Show

Vacation rentals with parking in Head of Hillsborough

Find vacation rentals that make arriving by car easier.

Waterview Cottage on Tracadie Bay - Bayview at Blue Heron - Head of Hillsborough

Waterview Cottage on Tracadie Bay - Bayview at Blue Heron

Cottage, Head of Hillsborough

Waterview Cottage on Tracadie Bay - Bayview at Blue Heron is a cottage in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

Read more

About Waterview Cottage on Tracadie Bay - Bayview at Blue Heron

Waterview Cottage on Tracadie Bay - Bayview at Blue Heron is a cottage in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,656.

From$379/night
Show
Shore to Sky Oceanfront Escape with Sunroom, Stunning Views & Beach Access - Head of Hillsborough

Shore to Sky Oceanfront Escape with Sunroom, Stunning Views & Beach Access

Holiday Home, Head of Hillsborough

Shore to Sky Oceanfront Escape with Sunroom, Stunning Views & Beach Access is a holiday home in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives…

Read more

About Shore to Sky Oceanfront Escape with Sunroom, Stunning Views & Beach Access

Shore to Sky Oceanfront Escape with Sunroom, Stunning Views & Beach Access is a holiday home in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $2,993.

From$428/night
Show
Blooming Point Beach House – Stunning Views, Beach Access, and Coastal Charm - Head of Hillsborough

Blooming Point Beach House – Stunning Views, Beach Access, and Coastal Charm

Holiday Home, Head of Hillsborough

Blooming Point Beach House – Stunning Views, Beach Access, and Coastal Charm is a holiday home in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives…

Read more

About Blooming Point Beach House – Stunning Views, Beach Access, and Coastal Charm

Blooming Point Beach House – Stunning Views, Beach Access, and Coastal Charm is a holiday home in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,054.

From$436/night
Show
Ocean Front Property, Nearby Beaches and Breathtaking Sunsets! - Head of Hillsborough

Ocean Front Property, Nearby Beaches and Breathtaking Sunsets!

Cottage, Head of Hillsborough

Ocean Front Property, Nearby Beaches and Breathtaking Sunsets! is a cottage in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About Ocean Front Property, Nearby Beaches and Breathtaking Sunsets!

Ocean Front Property, Nearby Beaches and Breathtaking Sunsets! is a cottage in Head of Hillsborough, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 10 - Sat, Oct 17 · 7 nights · total from $3,423.

From$489/night
Show