Vacation rentals in Pennfield

62 available vacation rental offers

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Best vacation rentals and Airbnb offers in Pennfield

Walk to Campobello & beach/Weekly discount/Pets welcome/Water views /Fire pit - Pennfield
10 ★ 72 reviews

Walk to Campobello & beach/Weekly discount/Pets welcome/Water views /Fire pit

Holiday Home, Pennfield

Walk to Campobello & beach/Weekly discount/Pets welcome/Water views /Fire pit is a holiday home in Pennfield, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Walk to Campobello & beach/Weekly discount/Pets welcome/Water views /Fire pit

Walk to Campobello & beach/Weekly discount/Pets welcome/Water views /Fire pit is a holiday home in Pennfield, 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,985.

From$284/night
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Beautiful 2BR loft with views of bay and Eastport harbor activity. - Pennfield
10 ★ 41 reviews

Beautiful 2BR loft with views of bay and Eastport harbor activity.

Condo, Pennfield

Beautiful 2BR loft with views of bay and Eastport harbor activity. is a condo in Pennfield, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Beautiful 2BR loft with views of bay and Eastport harbor activity.

Beautiful 2BR loft with views of bay and Eastport harbor activity. is a condo in Pennfield, 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,953.

From$279/night
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Carriage House on 9.5 Acres. Sit at the ocean or enjoy the waterfalls - Luxury - Pennfield
10 ★ 18 reviews

Carriage House on 9.5 Acres. Sit at the ocean or enjoy the waterfalls - Luxury

Holiday Home, Pennfield

Carriage House on 9.5 Acres. Sit at the ocean or enjoy the waterfalls - Luxury is a holiday home in Pennfield, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Carriage House on 9.5 Acres. Sit at the ocean or enjoy the waterfalls - Luxury

Carriage House on 9.5 Acres. Sit at the ocean or enjoy the waterfalls - Luxury is a holiday home in Pennfield, 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,961.

From$280/night
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The Roosters Cottage of Habour De Lute on Campobello Island - Pennfield
10 ★ 7 reviews

The Roosters Cottage of Habour De Lute on Campobello Island

Cottage, Pennfield

The Roosters Cottage of Habour De Lute on Campobello Island is a cottage in Pennfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Roosters Cottage of Habour De Lute on Campobello Island

The Roosters Cottage of Habour De Lute on Campobello Island is a cottage in Pennfield, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,180.

From$311/night
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Family-friendly vacation rentals in Pennfield

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

Blue Heron Cottage with waterfront - Pennfield
10 ★ 4 reviews

Blue Heron Cottage with waterfront

Cottage, Pennfield

Blue Heron Cottage with waterfront is a cottage in Pennfield, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Blue Heron Cottage with waterfront

Blue Heron Cottage with waterfront is a cottage in Pennfield, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,034.

From$291/night
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Stunning Maine cabin on Boyden Lake - Pennfield
9.8 ★ 27 reviews

Stunning Maine cabin on Boyden Lake

Cabin, Pennfield

Stunning Maine cabin on Boyden Lake is a cabin in Pennfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Stunning Maine cabin on Boyden Lake

Stunning Maine cabin on Boyden Lake is a cabin in Pennfield, with pet-friendly space 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,917.

From$417/night
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Amazing Views from Bay View Apartment at The Phoenix on Water Street - Pennfield
9.8 ★ 26 reviews

Amazing Views from Bay View Apartment at The Phoenix on Water Street

Apartment, Pennfield

Amazing Views from Bay View Apartment at The Phoenix on Water Street is a apartment in Pennfield, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Amazing Views from Bay View Apartment at The Phoenix on Water Street

Amazing Views from Bay View Apartment at The Phoenix on Water Street is a apartment in Pennfield, 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, kitchen, with kitchen, kids friendly, and kid friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,836.

From$405/night
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Private Oceanfront Cottage renovated: New Oceanfront Master BR for 2023 season - Pennfield
9.4 ★ 41 reviews

Private Oceanfront Cottage renovated: New Oceanfront Master BR for 2023 season

Cottage, Pennfield

Private Oceanfront Cottage renovated: New Oceanfront Master BR for 2023 season is a cottage in Pennfield, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About Private Oceanfront Cottage renovated: New Oceanfront Master BR for 2023 season

Private Oceanfront Cottage renovated: New Oceanfront Master BR for 2023 season is a cottage in Pennfield, 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 wifi, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,060.

From$437/night
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Pet-friendly vacation rentals in Pennfield

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

Colonels Quarters of Eastport - Pennfield
9.6 ★ 18 reviews

Colonels Quarters of Eastport

Holiday Home, Pennfield

Colonels Quarters of Eastport is a holiday home in Pennfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Colonels Quarters of Eastport

Colonels Quarters of Eastport is a holiday home in Pennfield, with pet-friendly space 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,397.

From$342/night
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Beautiful loft in heart of town, deck area with stunning views! - Pennfield
9.6 ★ 5 reviews

Beautiful loft in heart of town, deck area with stunning views!

Apartment, Pennfield

Beautiful loft in heart of town, deck area with stunning views! is a apartment in Pennfield, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a…

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About Beautiful loft in heart of town, deck area with stunning views!

Beautiful loft in heart of town, deck area with stunning views! is a apartment in Pennfield, with pet-friendly space, outdoor space, 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,436.

From$348/night
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Cozy Capen Cottage— easy access to downtown Eastport - Pennfield
9 ★ 4 reviews

Cozy Capen Cottage— easy access to downtown Eastport

Apartment, Pennfield

Cozy Capen Cottage— easy access to downtown Eastport is a apartment in Pennfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cozy Capen Cottage— easy access to downtown Eastport

Cozy Capen Cottage— easy access to downtown Eastport is a apartment in Pennfield, with pet-friendly space 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,921.

From$417/night
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Beach House Little Dipper Harbour Oceanfront Retreat - new property mgmt in 2026 - Pennfield
8 ★ 20 reviews

Beach House Little Dipper Harbour Oceanfront Retreat - new property mgmt in 2026

Holiday Home, Pennfield

Beach House Little Dipper Harbour Oceanfront Retreat - new property mgmt in 2026 is a holiday home in Pennfield, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Beach House Little Dipper Harbour Oceanfront Retreat - new property mgmt in 2026

Beach House Little Dipper Harbour Oceanfront Retreat - new property mgmt in 2026 is a holiday home in Pennfield, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,932.

From$419/night
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Vacation rentals with parking in Pennfield

Find vacation rentals that make arriving by car easier.

Cozy Maine Getaway: Covered Deck, Walk to Beach! - Pennfield
10 ★ 13 reviews

Cozy Maine Getaway: Covered Deck, Walk to Beach!

Condo, Pennfield

Cozy Maine Getaway: Covered Deck, Walk to Beach! is a condo in Pennfield, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

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About Cozy Maine Getaway: Covered Deck, Walk to Beach!

Cozy Maine Getaway: Covered Deck, Walk to Beach! is a condo in Pennfield, with easy beach access, outdoor space, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,307.

From$330/night
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Ebb Tide- \"Magical by Nature\" - Pennfield
10 ★ 6 reviews

Ebb Tide- \"Magical by Nature\"

Holiday Home, Pennfield

Ebb Tide- \"Magical by Nature\" is a holiday home in Pennfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Ebb Tide- \"Magical by Nature\"

Ebb Tide- \"Magical by Nature\" is a holiday home in Pennfield, 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 free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,593.

From$370/night
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Cozy Maine Getaway: Covered Deck, Walk to Beach! - Pennfield
10 ★ 1 reviews

Cozy Maine Getaway: Covered Deck, Walk to Beach!

Apartment, Pennfield

Cozy Maine Getaway: Covered Deck, Walk to Beach! is a apartment in Pennfield, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Cozy Maine Getaway: Covered Deck, Walk to Beach!

Cozy Maine Getaway: Covered Deck, Walk to Beach! is a apartment in Pennfield, with easy beach access, outdoor space, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,667.

From$311/night
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Stay at 'The Manse' in Historic St. Andrews - Pennfield
9.8 ★ 17 reviews

Stay at 'The Manse' in Historic St. Andrews

Holiday Home, Pennfield

Stay at 'The Manse' in Historic St. Andrews is a holiday home in Pennfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Stay at 'The Manse' in Historic St. Andrews

Stay at 'The Manse' in Historic St. Andrews is a holiday home in Pennfield, 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 free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,698.

From$385/night
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Vacation rentals with a kitchen in Pennfield

Compare stays with kitchen access for longer trips and easier meals.

The Driftwood, Saint Andrews - Pennfield
10 ★ 1 reviews

The Driftwood, Saint Andrews

Holiday Home, Pennfield

The Driftwood, Saint Andrews is a holiday home in Pennfield, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Driftwood, Saint Andrews

The Driftwood, Saint Andrews is a holiday home in Pennfield, with 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,959.

From$423/night
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Water front house. A deck you will not want to leave! - Pennfield
9.8 ★ 29 reviews

Water front house. A deck you will not want to leave!

Holiday Home, Pennfield

Water front house. A deck you will not want to leave! is a holiday home in Pennfield, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Water front house. A deck you will not want to leave!

Water front house. A deck you will not want to leave! is a holiday home in Pennfield, with outdoor space, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,792.

From$399/night
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SANDY'S BEACHFRONT CABIN B visit eastern most point in US 1 mile by state park - Pennfield
9.8 ★ 7 reviews

SANDY'S BEACHFRONT CABIN B visit eastern most point in US 1 mile by state park

Cabin, Pennfield

SANDY'S BEACHFRONT CABIN B visit eastern most point in US 1 mile by state park is a cabin in Pennfield, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About SANDY'S BEACHFRONT CABIN B visit eastern most point in US 1 mile by state park

SANDY'S BEACHFRONT CABIN B visit eastern most point in US 1 mile by state park is a cabin in Pennfield, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,708.

From$387/night
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Bayside Cabin set on the edge of Cobscook Bay facing the beautiful Sunset! - Pennfield
6 ★ 1 reviews

Bayside Cabin set on the edge of Cobscook Bay facing the beautiful Sunset!

Cabin, Pennfield

Bayside Cabin set on the edge of Cobscook Bay facing the beautiful Sunset! is a cabin in Pennfield, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Bayside Cabin set on the edge of Cobscook Bay facing the beautiful Sunset!

Bayside Cabin set on the edge of Cobscook Bay facing the beautiful Sunset! is a cabin in Pennfield, 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,149.

From$164/night
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Top-rated vacation rentals in Pennfield

Explore guest-loved stays with strong review signals.

Spacious NY Style Loft Downtown Eastport - Pennfield
10 ★ 49 reviews

Spacious NY Style Loft Downtown Eastport

Condo, Pennfield

Spacious NY Style Loft Downtown Eastport is a condo in Pennfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Spacious NY Style Loft Downtown Eastport

Spacious NY Style Loft Downtown Eastport is a condo in Pennfield, with pet-friendly space 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,211.

From$459/night
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Lubec Saltbox with sunsets!! Guests give us 10/10 REVIEWS!!! - Pennfield
10 ★ 21 reviews

Lubec Saltbox with sunsets!! Guests give us 10/10 REVIEWS!!!

Holiday Home, Pennfield

Lubec Saltbox with sunsets!! Guests give us 10/10 REVIEWS!!! is a holiday home in Pennfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Lubec Saltbox with sunsets!! Guests give us 10/10 REVIEWS!!!

Lubec Saltbox with sunsets!! Guests give us 10/10 REVIEWS!!! is a holiday home in Pennfield, with pet-friendly space 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, pet friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,019.

From$431/night
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Luxury w/FIRE PIT, HOT TUB, KAYAKS by the water! PEACEFUL, PRIVATE & THE VIEW! - Pennfield
10 ★ 6 reviews

Luxury w/FIRE PIT, HOT TUB, KAYAKS by the water! PEACEFUL, PRIVATE & THE VIEW!

Apartment, Pennfield

Luxury w/FIRE PIT, HOT TUB, KAYAKS by the water! PEACEFUL, PRIVATE & THE VIEW! is a apartment in Pennfield, with parking. This stay gives travelers a comfortable base for exploring the…

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About Luxury w/FIRE PIT, HOT TUB, KAYAKS by the water! PEACEFUL, PRIVATE & THE VIEW!

Luxury w/FIRE PIT, HOT TUB, KAYAKS by the water! PEACEFUL, PRIVATE & THE VIEW! is a apartment in Pennfield, 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, hot tub, parking, free parking, and ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,935.

From$419/night
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Ocean Sunsets and More! See Beautiful Johnson's Bay - Pennfield
9.8 ★ 27 reviews

Ocean Sunsets and More! See Beautiful Johnson's Bay

Apartment, Pennfield

Ocean Sunsets and More! See Beautiful Johnson's Bay is a apartment in Pennfield, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Ocean Sunsets and More! See Beautiful Johnson's Bay

Ocean Sunsets and More! See Beautiful Johnson's Bay is a apartment in Pennfield, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,977.

From$425/night
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