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.

Holiday Rentals in Jaffrey

Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
50 rentals in Jaffrey.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Charming Jaffrey Cottage w/ Mount Monadnock Views!, holiday rental in Jaffrey
Charming Jaffrey Cottage w/ Mount Monadnock Views!, holiday rental in Jaffrey
Charming Jaffrey Cottage w/ Mount Monadnock Views!, holiday rental in Jaffrey

Charming Jaffrey Cottage w/ Mount Monadnock Views!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Lakefront all-season beauty and fun!, holiday rental in Jaffrey
Lakefront all-season beauty and fun!, holiday rental in Jaffrey
Lakefront all-season beauty and fun!, holiday rental in Jaffrey

Lakefront all-season beauty and fun!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Amazing Mid-Century Modern Mountain Top Home on 160 Acres, holiday rental in Jaffrey
Amazing Mid-Century Modern Mountain Top Home on 160 Acres, holiday rental in Jaffrey
Amazing Mid-Century Modern Mountain Top Home on 160 Acres, holiday rental in Jaffrey

Amazing Mid-Century Modern Mountain Top Home on 160 Acres

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Waterfront New Englander Mt. Monadnock, holiday rental in Jaffrey
Waterfront New Englander Mt. Monadnock, holiday rental in Jaffrey
Waterfront New Englander Mt. Monadnock, holiday rental in Jaffrey

Waterfront New Englander Mt. Monadnock

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Jaffrey
Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Jaffrey
Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, holiday rental in Jaffrey

Sprawling, secluded gourmand's large cottage at base of Mt Monadnock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

NEW! Peaceful Waterfront Cottage By Mt Monadnock, holiday rental in Jaffrey
NEW! Peaceful Waterfront Cottage By Mt Monadnock, holiday rental in Jaffrey
NEW! Peaceful Waterfront Cottage By Mt Monadnock, holiday rental in Jaffrey

NEW! Peaceful Waterfront Cottage By Mt Monadnock

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!, holiday rental in Jaffrey
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!, holiday rental in Jaffrey
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!, holiday rental in Jaffrey

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
More info
Check-in
Check-out

Spacious lakefront cottage and guesthouse with all the comforts of home, holiday rental in Jaffrey
Spacious lakefront cottage and guesthouse with all the comforts of home, holiday rental in Jaffrey
Spacious lakefront cottage and guesthouse with all the comforts of home, holiday rental in Jaffrey

Spacious lakefront cottage and guesthouse with all the comforts of home

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Waterfont log home nestled in the pines, holiday rental in Jaffrey
Waterfont log home nestled in the pines, holiday rental in Jaffrey
Waterfont log home nestled in the pines, holiday rental in Jaffrey

Waterfont log home nestled in the pines

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, holiday rental in Jaffrey
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, holiday rental in Jaffrey
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, holiday rental in Jaffrey

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Save time - get the best Jaffrey rentals sent straight to your email!
Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Jaffrey
Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Jaffrey
Secluded Architect designed House - Monadnock Region - Great Escape, holiday rental in Jaffrey

Secluded Architect designed House - Monadnock Region - Great Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Cobb Hill Estate - 6 bedroom house sleeps 15 on 750 acre property!, holiday rental in Jaffrey
Cobb Hill Estate - 6 bedroom house sleeps 15 on 750 acre property!, holiday rental in Jaffrey
Cobb Hill Estate - 6 bedroom house sleeps 15 on 750 acre property!, holiday rental in Jaffrey

Cobb Hill Estate - 6 bedroom house sleeps 15 on 750 acre property!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Check-in
Check-out

Secluded Vacation Home with direct lake frontage  on Contoocook Lake in NH, holiday rental in Jaffrey
Secluded Vacation Home with direct lake frontage  on Contoocook Lake in NH, holiday rental in Jaffrey
Secluded Vacation Home with direct lake frontage  on Contoocook Lake in NH, holiday rental in Jaffrey

Secluded Vacation Home with direct lake frontage on Contoocook Lake in NH

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!, holiday rental in Jaffrey
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!, holiday rental in Jaffrey
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!, holiday rental in Jaffrey

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake, holiday rental in Jaffrey
Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake, holiday rental in Jaffrey
Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake, holiday rental in Jaffrey

Retreat or Reunion Home with Grand Porch and Views of Mountain and Lake

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 19
Match: Sleeps
More info
Check-in
Check-out

Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!, holiday rental in Jaffrey
Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!, holiday rental in Jaffrey
Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!, holiday rental in Jaffrey

Authentic Red Farm House On Zephyr Lake, Beautiful In All Seasons!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Vacationer's oasis on the waterfront of picturesque Pearly Pond., holiday rental in Jaffrey
Vacationer's oasis on the waterfront of picturesque Pearly Pond., holiday rental in Jaffrey
Vacationer's oasis on the waterfront of picturesque Pearly Pond., holiday rental in Jaffrey

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Relaxing lake front, big deck, sandy beach, holiday rental in Jaffrey
Relaxing lake front, big deck, sandy beach, holiday rental in Jaffrey
Relaxing lake front, big deck, sandy beach, holiday rental in Jaffrey

Relaxing lake front, big deck, sandy beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Cozy, Wooded, Waterfront, Mountain View Cabin on Silver Lake, holiday rental in Jaffrey
Cozy, Wooded, Waterfront, Mountain View Cabin on Silver Lake, holiday rental in Jaffrey
Cozy, Wooded, Waterfront, Mountain View Cabin on Silver Lake, holiday rental in Jaffrey

Cozy, Wooded, Waterfront, Mountain View Cabin on Silver Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Cottage Country Get Away, holiday rental in Jaffrey
Cottage Country Get Away, holiday rental in Jaffrey
Cottage Country Get Away, holiday rental in Jaffrey

Cottage Country Get Away

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Lakeside Family Fun!!, holiday rental in Jaffrey
Lakeside Family Fun!!, holiday rental in Jaffrey
Lakeside Family Fun!!, holiday rental in Jaffrey

Lakeside Family Fun!!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Beautiful Home On Lake Skatutakee...Historic Harrisville NH, holiday rental in Jaffrey
Beautiful Home On Lake Skatutakee...Historic Harrisville NH, holiday rental in Jaffrey
Beautiful Home On Lake Skatutakee...Historic Harrisville NH, holiday rental in Jaffrey

Beautiful Home On Lake Skatutakee...Historic Harrisville NH

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Lemon Drop Cottage a private cottage getaway, holiday rental in Jaffrey
Lemon Drop Cottage a private cottage getaway, holiday rental in Jaffrey
Lemon Drop Cottage a private cottage getaway, holiday rental in Jaffrey

Lemon Drop Cottage a private cottage getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

5 Bedroom cozy New England home - Cobb Meadow House, holiday rental in Jaffrey
5 Bedroom cozy New England home - Cobb Meadow House, holiday rental in Jaffrey
5 Bedroom cozy New England home - Cobb Meadow House, holiday rental in Jaffrey

5 Bedroom cozy New England home - Cobb Meadow House

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Inviting Lakeside Comfort in Historic Harrisville, holiday rental in Jaffrey
Inviting Lakeside Comfort in Historic Harrisville, holiday rental in Jaffrey
Inviting Lakeside Comfort in Historic Harrisville, holiday rental in Jaffrey

Inviting Lakeside Comfort in Historic Harrisville

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Classic Lakefront Family Summer Home, holiday rental in Jaffrey
Classic Lakefront Family Summer Home, holiday rental in Jaffrey
Classic Lakefront Family Summer Home, holiday rental in Jaffrey

Classic Lakefront Family Summer Home

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out

Large home for families or groups, holiday rental in Jaffrey
Large home for families or groups, holiday rental in Jaffrey
Large home for families or groups, holiday rental in Jaffrey

Large home for families or groups

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out

Charming Waterfront Log Cabin w/ Private Island, holiday rental in Jaffrey
Charming Waterfront Log Cabin w/ Private Island, holiday rental in Jaffrey
Charming Waterfront Log Cabin w/ Private Island, holiday rental in Jaffrey

Charming Waterfront Log Cabin w/ Private Island

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

*NEW* Spectacular lake house with private dock, beach area & gorgeous views, holiday rental in Jaffrey
*NEW* Spectacular lake house with private dock, beach area & gorgeous views, holiday rental in Jaffrey
*NEW* Spectacular lake house with private dock, beach area & gorgeous views, holiday rental in Jaffrey

*NEW* Spectacular lake house with private dock, beach area & gorgeous views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out

Cozy Updated Log Cabin with Mountain Views close to Monadnock, holiday rental in Jaffrey
Cozy Updated Log Cabin with Mountain Views close to Monadnock, holiday rental in Jaffrey
Cozy Updated Log Cabin with Mountain Views close to Monadnock, holiday rental in Jaffrey

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!, holiday rental in Jaffrey
Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!, holiday rental in Jaffrey
Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!, holiday rental in Jaffrey

Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Off-Grid  Camp,  Lakeside Cottage, holiday rental in Jaffrey
Off-Grid  Camp,  Lakeside Cottage, holiday rental in Jaffrey
Off-Grid  Camp,  Lakeside Cottage, holiday rental in Jaffrey

Off-Grid Camp, Lakeside Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Skywood - - Dublin, NH, holiday rental in Jaffrey
Skywood - - Dublin, NH, holiday rental in Jaffrey
Skywood - - Dublin, NH, holiday rental in Jaffrey

Skywood - - Dublin, NH

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
More info
Check-in
Check-out

Hemlock House at Aldworth Manor, holiday rental in Jaffrey
Hemlock House at Aldworth Manor, holiday rental in Jaffrey
Hemlock House at Aldworth Manor, holiday rental in Jaffrey

Hemlock House at Aldworth Manor

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out

Rustic Lodge on Blueberry Mountain, holiday rental in Jaffrey
Rustic Lodge on Blueberry Mountain, holiday rental in Jaffrey
Rustic Lodge on Blueberry Mountain, holiday rental in Jaffrey

Rustic Lodge on Blueberry Mountain

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Enjoy your stay in an antique home in an antique toy museum!, holiday rental in Jaffrey
Enjoy your stay in an antique home in an antique toy museum!, holiday rental in Jaffrey
Enjoy your stay in an antique home in an antique toy museum!, holiday rental in Jaffrey

Enjoy your stay in an antique home in an antique toy museum!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Lakeside Lodge with Rock Fireplace, holiday rental in Jaffrey
Lakeside Lodge with Rock Fireplace, holiday rental in Jaffrey
Lakeside Lodge with Rock Fireplace, holiday rental in Jaffrey

Lakeside Lodge with Rock Fireplace

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Renovated Cottage w/spectacular mountain view, holiday rental in Jaffrey
Renovated Cottage w/spectacular mountain view, holiday rental in Jaffrey
Renovated Cottage w/spectacular mountain view, holiday rental in Jaffrey

Renovated Cottage w/spectacular mountain view

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Entire house on privately situated Lilac Hill abuts conservation land, holiday rental in Jaffrey
Entire house on privately situated Lilac Hill abuts conservation land, holiday rental in Jaffrey
Entire house on privately situated Lilac Hill abuts conservation land, holiday rental in Jaffrey

Entire house on privately situated Lilac Hill abuts conservation land

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Large, Sunny House with Babbling Brook in Country Setting ; Close to Skiing, holiday rental in Jaffrey
Large, Sunny House with Babbling Brook in Country Setting ; Close to Skiing, holiday rental in Jaffrey
Large, Sunny House with Babbling Brook in Country Setting ; Close to Skiing, holiday rental in Jaffrey

Large, Sunny House with Babbling Brook in Country Setting ; Close to Skiing

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Spectacular Waterfront Modern Lake House on Nubanusit Lake, Southern NH, holiday rental in Jaffrey
Spectacular Waterfront Modern Lake House on Nubanusit Lake, Southern NH, holiday rental in Jaffrey
Spectacular Waterfront Modern Lake House on Nubanusit Lake, Southern NH, holiday rental in Jaffrey

Spectacular Waterfront Modern Lake House on Nubanusit Lake, Southern NH

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out

Cozy Lakefront Cottage, holiday rental in Jaffrey
Cozy Lakefront Cottage, holiday rental in Jaffrey
Cozy Lakefront Cottage, holiday rental in Jaffrey

Cozy Lakefront Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Waterfront house 2020, holiday rental in Jaffrey
Waterfront house 2020, holiday rental in Jaffrey
Waterfront house 2020, holiday rental in Jaffrey

Waterfront house 2020

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna, holiday rental in Jaffrey
Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna, holiday rental in Jaffrey
Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna, holiday rental in Jaffrey

Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Lake House on walking trail near Mount Monadnock, holiday rental in Jaffrey
Lake House on walking trail near Mount Monadnock, holiday rental in Jaffrey
Lake House on walking trail near Mount Monadnock, holiday rental in Jaffrey

Lake House on walking trail near Mount Monadnock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

Cottage on Laurel Lake, Private lake access, picture perfect sunsets, holiday rental in Jaffrey
Cottage on Laurel Lake, Private lake access, picture perfect sunsets, holiday rental in Jaffrey
Cottage on Laurel Lake, Private lake access, picture perfect sunsets, holiday rental in Jaffrey

Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Visit us in Harrisville, NH and have plenty of beds, holiday rental in Jaffrey
Visit us in Harrisville, NH and have plenty of beds, holiday rental in Jaffrey
Visit us in Harrisville, NH and have plenty of beds, holiday rental in Jaffrey

Visit us in Harrisville, NH and have plenty of beds

Holiday Rental House
11 bedrooms
3 bathrooms
Sleeps 22
Match: Sleeps
More info
Check-in
Check-out

A spacious one bedroom apartment on a family farm in beautiful Monadnock Region., holiday rental in Jaffrey
A spacious one bedroom apartment on a family farm in beautiful Monadnock Region., holiday rental in Jaffrey
A spacious one bedroom apartment on a family farm in beautiful Monadnock Region., holiday rental in Jaffrey

A spacious one bedroom apartment on a family farm in beautiful Monadnock Region.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Cabin on clean lake with great deck and dock, holiday rental in Jaffrey
Cabin on clean lake with great deck and dock, holiday rental in Jaffrey
Cabin on clean lake with great deck and dock, holiday rental in Jaffrey

Cabin on clean lake with great deck and dock

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!, holiday rental in Jaffrey
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!, holiday rental in Jaffrey
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!, holiday rental in Jaffrey

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out

PreviousNext
1
Frequently Asked Questions about Jaffrey