We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Hillsborough Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Hillsborough.
Cozy Lakeside Year Round Retreat ☀️ � � � � � �� ❄️  � welcome �, vacation rental in Hillsborough
Cozy Lakeside Year Round Retreat ☀️ � � � � � �� ❄️  � welcome �, vacation rental in Hillsborough
Cozy Lakeside Year Round Retreat ☀️ � � � � � �� ❄️  � welcome �, vacation rental in Hillsborough

Cozy Lakeside Year Round Retreat ☀️ � � � � � �� ❄️ � welcome �

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Hillsborough
The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Hillsborough
The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Hillsborough

The Rustic Retreat - Lakefront Cottage on Franklin Pierce Lake!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Hillsborough Village Retreat: Walk to River!, vacation rental in Hillsborough
Hillsborough Village Retreat: Walk to River!, vacation rental in Hillsborough
Hillsborough Village Retreat: Walk to River!, vacation rental in Hillsborough

Hillsborough Village Retreat: Walk to River!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cabin in the Woods, vacation rental in Hillsborough
Cabin in the Woods, vacation rental in Hillsborough
Cabin in the Woods, vacation rental in Hillsborough

Cabin in the Woods

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakefront Getaway w/ Canoe & Dock Fishing!, vacation rental in Hillsborough
Lakefront Getaway w/ Canoe & Dock Fishing!, vacation rental in Hillsborough
Lakefront Getaway w/ Canoe & Dock Fishing!, vacation rental in Hillsborough

Lakefront Getaway w/ Canoe & Dock Fishing!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Emerald Lake Cottage Under the Pines, vacation rental in Hillsborough
Emerald Lake Cottage Under the Pines, vacation rental in Hillsborough
Emerald Lake Cottage Under the Pines, vacation rental in Hillsborough

Emerald Lake Cottage Under the Pines

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Available summer and fall 2023 - Beautiful Waterfront Cottage (4 BR), vacation rental in Hillsborough
Available summer and fall 2023 - Beautiful Waterfront Cottage (4 BR), vacation rental in Hillsborough
Available summer and fall 2023 - Beautiful Waterfront Cottage (4 BR), vacation rental in Hillsborough

Available summer and fall 2023 - Beautiful Waterfront Cottage (4 BR)

Rental Home
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse., vacation rental in Hillsborough
Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse., vacation rental in Hillsborough
Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse., vacation rental in Hillsborough

Stone Pond Farm sleeps 9, peaceful, family friendly, quaint country farmhouse.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Modern CozyRustic House w Hot Tub & Pool Table near Pond/Ski, vacation rental in Hillsborough
Modern CozyRustic House w Hot Tub & Pool Table near Pond/Ski, vacation rental in Hillsborough
Modern CozyRustic House w Hot Tub & Pool Table near Pond/Ski, vacation rental in Hillsborough

Modern CozyRustic House w Hot Tub & Pool Table near Pond/Ski

Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
All Season Lake House, vacation rental in Hillsborough
All Season Lake House, vacation rental in Hillsborough
All Season Lake House, vacation rental in Hillsborough

All Season Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The following properties within 20 miles of Hillsborough match all your filters:
Cozy Cottage on Quiet Lake, vacation rental in Hillsborough
Cozy Cottage on Quiet Lake, vacation rental in Hillsborough
Cozy Cottage on Quiet Lake, vacation rental in Hillsborough

Cozy Cottage on Quiet Lake

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Large, Comfy Family House w/ Lake & Beach access, vacation rental in Hillsborough
Large, Comfy Family House w/ Lake & Beach access, vacation rental in Hillsborough
Large, Comfy Family House w/ Lake & Beach access, vacation rental in Hillsborough

Large, Comfy Family House w/ Lake & Beach access

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lake Front Retreat With Deep Water Dock, vacation rental in Hillsborough
Lake Front Retreat With Deep Water Dock, vacation rental in Hillsborough
Lake Front Retreat With Deep Water Dock, vacation rental in Hillsborough

Lake Front Retreat With Deep Water Dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Peaceful Waterfront Cottage, vacation rental in Hillsborough
Peaceful Waterfront Cottage, vacation rental in Hillsborough
Peaceful Waterfront Cottage, vacation rental in Hillsborough

Peaceful Waterfront Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming log cabin 'Lake Escape' on Highland Lake in Stoddard, NH....., vacation rental in Hillsborough
Charming log cabin 'Lake Escape' on Highland Lake in Stoddard, NH....., vacation rental in Hillsborough
Charming log cabin 'Lake Escape' on Highland Lake in Stoddard, NH....., vacation rental in Hillsborough

Charming log cabin 'Lake Escape' on Highland Lake in Stoddard, NH.....

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Pristine Waterfront, Charming Home, Breathtaking Views, vacation rental in Hillsborough
Pristine Waterfront, Charming Home, Breathtaking Views, vacation rental in Hillsborough
Pristine Waterfront, Charming Home, Breathtaking Views, vacation rental in Hillsborough

Pristine Waterfront, Charming Home, Breathtaking Views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious Family Lake & Ski House, vacation rental in Hillsborough
Spacious Family Lake & Ski House, vacation rental in Hillsborough
Spacious Family Lake & Ski House, vacation rental in Hillsborough

Spacious Family Lake & Ski House

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Outdoor Playground on Lake and Close to Skiing, vacation rental in Hillsborough
Outdoor Playground on Lake and Close to Skiing, vacation rental in Hillsborough
Outdoor Playground on Lake and Close to Skiing, vacation rental in Hillsborough

Outdoor Playground on Lake and Close to Skiing

Rental Home
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury Hot Tub Getaway, vacation rental in Hillsborough
Luxury Hot Tub Getaway, vacation rental in Hillsborough
Luxury Hot Tub Getaway, vacation rental in Hillsborough

Luxury Hot Tub Getaway

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Camp Nestled in the Woods, vacation rental in Hillsborough
Cozy Camp Nestled in the Woods, vacation rental in Hillsborough
Cozy Camp Nestled in the Woods, vacation rental in Hillsborough

Cozy Camp Nestled in the Woods

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Special Rates! Lakefront Cottage in a Quiet, Beautiful Location, vacation rental in Hillsborough
Special Rates! Lakefront Cottage in a Quiet, Beautiful Location, vacation rental in Hillsborough
Special Rates! Lakefront Cottage in a Quiet, Beautiful Location, vacation rental in Hillsborough

Special Rates! Lakefront Cottage in a Quiet, Beautiful Location

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Deer Valley Retreat, Lovely Log Cabin, vacation rental in Hillsborough
Deer Valley Retreat, Lovely Log Cabin, vacation rental in Hillsborough
Deer Valley Retreat, Lovely Log Cabin, vacation rental in Hillsborough

Deer Valley Retreat, Lovely Log Cabin

Cabin
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Little Red Wing - 1950's Lake cottage, vacation rental in Hillsborough
Little Red Wing - 1950's Lake cottage, vacation rental in Hillsborough
Little Red Wing - 1950's Lake cottage, vacation rental in Hillsborough

Little Red Wing - 1950's Lake cottage

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Waterfront Cottage with Large Dock, vacation rental in Hillsborough
Waterfront Cottage with Large Dock, vacation rental in Hillsborough
Waterfront Cottage with Large Dock, vacation rental in Hillsborough

Waterfront Cottage with Large Dock

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Hillsborough
Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Hillsborough
Lakefront Cottage on Franklin Pierce Lake!, vacation rental in Hillsborough

Lakefront Cottage on Franklin Pierce Lake!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious, quiet country retreat, vacation rental in Hillsborough
Spacious, quiet country retreat, vacation rental in Hillsborough
Spacious, quiet country retreat, vacation rental in Hillsborough

Spacious, quiet country retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Private Hot Tub Suite, vacation rental in Hillsborough
Private Hot Tub Suite, vacation rental in Hillsborough
Private Hot Tub Suite, vacation rental in Hillsborough

Private Hot Tub Suite

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Henniker Vacation Rental Near Ski Area!, vacation rental in Hillsborough
Cozy Henniker Vacation Rental Near Ski Area!, vacation rental in Hillsborough
Cozy Henniker Vacation Rental Near Ski Area!, vacation rental in Hillsborough

Cozy Henniker Vacation Rental Near Ski Area!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Direct Waterfront, Year-Round, A-Frame Cabin, vacation rental in Hillsborough
Direct Waterfront, Year-Round, A-Frame Cabin, vacation rental in Hillsborough
Direct Waterfront, Year-Round, A-Frame Cabin, vacation rental in Hillsborough

Direct Waterfront, Year-Round, A-Frame Cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!, vacation rental in Hillsborough
Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!, vacation rental in Hillsborough
Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!, vacation rental in Hillsborough

Rustic Bradford Cottage - 14 Miles to Sunapee Mtn!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakefront Cottage on Peaceful Horace Lake, vacation rental in Hillsborough
Lakefront Cottage on Peaceful Horace Lake, vacation rental in Hillsborough
Lakefront Cottage on Peaceful Horace Lake, vacation rental in Hillsborough

Lakefront Cottage on Peaceful Horace Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Highland Lake Waterfront Cabin, vacation rental in Hillsborough
Highland Lake Waterfront Cabin, vacation rental in Hillsborough
Highland Lake Waterfront Cabin, vacation rental in Hillsborough

Highland Lake Waterfront Cabin

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Rustic Updated Cozy Lake House! Close to skiing!, vacation rental in Hillsborough
Rustic Updated Cozy Lake House! Close to skiing!, vacation rental in Hillsborough
Rustic Updated Cozy Lake House! Close to skiing!, vacation rental in Hillsborough

Rustic Updated Cozy Lake House! Close to skiing!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
"The Only One on Earth", vacation rental in Hillsborough
"The Only One on Earth", vacation rental in Hillsborough
"The Only One on Earth", vacation rental in Hillsborough

"The Only One on Earth"

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cabin: Private Hot Tub, Walk to Pats Peak Ski Area, vacation rental in Hillsborough
Cabin: Private Hot Tub, Walk to Pats Peak Ski Area, vacation rental in Hillsborough
Cabin: Private Hot Tub, Walk to Pats Peak Ski Area, vacation rental in Hillsborough

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
NH Hidden Gem !!, vacation rental in Hillsborough
NH Hidden Gem !!, vacation rental in Hillsborough
NH Hidden Gem !!, vacation rental in Hillsborough

NH Hidden Gem !!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
King Bed in Washington, NH - A Tranquil Retreat, vacation rental in Hillsborough
King Bed in Washington, NH - A Tranquil Retreat, vacation rental in Hillsborough
King Bed in Washington, NH - A Tranquil Retreat, vacation rental in Hillsborough

King Bed in Washington, NH - A Tranquil Retreat

Rental Home
4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Washington Vacation Rental w/ Lake Access & Grill!, vacation rental in Hillsborough
Washington Vacation Rental w/ Lake Access & Grill!, vacation rental in Hillsborough
Washington Vacation Rental w/ Lake Access & Grill!, vacation rental in Hillsborough

Washington Vacation Rental w/ Lake Access & Grill!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 lakefront cottages on Franklin Pierce Lake, vacation rental in Hillsborough
2 lakefront cottages on Franklin Pierce Lake, vacation rental in Hillsborough
2 lakefront cottages on Franklin Pierce Lake, vacation rental in Hillsborough

2 lakefront cottages on Franklin Pierce Lake

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Private Lakehouse Getaway for relaxing and fun!, vacation rental in Hillsborough
Private Lakehouse Getaway for relaxing and fun!, vacation rental in Hillsborough
Private Lakehouse Getaway for relaxing and fun!, vacation rental in Hillsborough

Private Lakehouse Getaway for relaxing and fun!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spectacular Log Home with Private Lake Access, vacation rental in Hillsborough
Spectacular Log Home with Private Lake Access, vacation rental in Hillsborough
Spectacular Log Home with Private Lake Access, vacation rental in Hillsborough

Spectacular Log Home with Private Lake Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Welcoming New Hampshire Home on ~ 3 Acres!, vacation rental in Hillsborough
Welcoming New Hampshire Home on ~ 3 Acres!, vacation rental in Hillsborough
Welcoming New Hampshire Home on ~ 3 Acres!, vacation rental in Hillsborough

Welcoming New Hampshire Home on ~ 3 Acres!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Iona Lake House on Lake Massasecum, vacation rental in Hillsborough
Iona Lake House on Lake Massasecum, vacation rental in Hillsborough
Iona Lake House on Lake Massasecum, vacation rental in Hillsborough

Iona Lake House on Lake Massasecum

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Highland Lake Waterfront home perfect for family, fun, outdoors, and S’Mores!, vacation rental in Hillsborough
Highland Lake Waterfront home perfect for family, fun, outdoors, and S’Mores!, vacation rental in Hillsborough
Highland Lake Waterfront home perfect for family, fun, outdoors, and S’Mores!, vacation rental in Hillsborough

Highland Lake Waterfront home perfect for family, fun, outdoors, and S’Mores!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious, Sunny Lake House. Close to ski trails., vacation rental in Hillsborough
Spacious, Sunny Lake House. Close to ski trails., vacation rental in Hillsborough
Spacious, Sunny Lake House. Close to ski trails., vacation rental in Hillsborough

Spacious, Sunny Lake House. Close to ski trails.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!, vacation rental in Hillsborough
Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!, vacation rental in Hillsborough
Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!, vacation rental in Hillsborough

Grey Heron Lake House- Super Cozy Family Guest Home Right on the Water!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Escape to Lakeside Country Home in New Hampshire, vacation rental in Hillsborough
Escape to Lakeside Country Home in New Hampshire, vacation rental in Hillsborough
Escape to Lakeside Country Home in New Hampshire, vacation rental in Hillsborough

Escape to Lakeside Country Home in New Hampshire

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Redwood, vacation rental in Hillsborough
Redwood, vacation rental in Hillsborough
Redwood, vacation rental in Hillsborough

Redwood

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The 1823 Farmhouse at the base of Pat's Peak, vacation rental in Hillsborough
The 1823 Farmhouse at the base of Pat's Peak, vacation rental in Hillsborough
The 1823 Farmhouse at the base of Pat's Peak, vacation rental in Hillsborough

The 1823 Farmhouse at the base of Pat's Peak

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lakefront Luxury Home on Horace Lake, vacation rental in Hillsborough
Lakefront Luxury Home on Horace Lake, vacation rental in Hillsborough
Lakefront Luxury Home on Horace Lake, vacation rental in Hillsborough

Lakefront Luxury Home on Horace Lake

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Showing results 1-50 of 50
Frequently Asked Questions about Hillsborough